I’ve been using Dropbox for a quite some time now, and was recently reminded of a compelling reason to finally recommend it to you.
One of the common questions I get is “how do I share [files, photos, documents, whatever] with my [friends, business associates, contacts] without using email, and without having them show up on the public internet?”
Dropbox solves that, and a lot more.
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Dropbox basics
Here’s the basic idea behind Dropbox: I create an account on Dropbox, and install the Dropbox software on two machines: A and B. On each, I point the Dropbox software at a folder to keep synchronized between the two machines.
It does.
It’s that simple.
Files I place in my Dropbox folder on machine A shortly appear in machine B’s Dropbox folder. “Shortly” depends on the speed of your internet connection and the size of the file, but that’s the fundamental operation: update a file on machine A, and Dropbox updates it on machine B. Add a file to B, it shows up on A. Create a folder on A and the folder appears on B.
That alone is a very powerful concept if you have more than one machine. Imagine simply keeping your documents automatically copied between several machines.
Now, based on that simple concept, we start adding features for different scenarios.
Dropbox for backup
You don’t need machine “B”.
Dropbox also makes the files you place in that folder accessible via your account on the Dropbox web site. It’s a great way to back up important documents off-site.
One approach is to make your Dropbox folder your “working” folder. I do this for the books I write as I’m writing them. I store the manuscript I’m working on in my Dropbox folder. Every time I save, or exit the editor, the files are updated on my hard disk. Each time they’re updated on disk, they’re uploaded to the web.
Offsite storage without a second thought.
Dropbox for data transfer
Machines “A” and “B” need not be in the same place.
Dropbox works across the internet, so if machine A and machine B are in two different places (but connected to the internet), then Dropbox continues to keep the folder contents in sync.
I do this all the time, simply as a side effect of having my desktop machine and my laptop both set up with Dropbox. When I’m travelling – be it a short trip to the local coffee shop, or a longer trip out of town, each time I place or update a file in my Dropbox on my laptop, it shows up on my machine at home a few minutes later.
Dropbox for collaboration
Machines “A” and “B” need not both be your machines.
You can share folders within your Dropbox with other Dropbox users. Place a file in a shared folder, and only those users you give access to will have access to those files – in their Dropbox account.
As I work with my assistants, we often share files this way. I have folders in my Dropbox setup that are dedicated to sharing with each. If I want to send one assistant a file, or maintain a reference copy of something for her, I simply drop it into her folder in my Dropbox. A few minutes later it shows up in the “Leo” folder on her Dropbox installation.
I find Dropbox to be the perfect solution for the file sharing needed.
Dropbox for sharing
Machine “B” doesn’t need to exist – again.
Have a file you want to share with the world? Drop it into your Dropbox, right click on it, and choose “Copy Public Link”. The result? A public link: a link that you can give to anyone, whether they have a Dropbox account or not.
For example, here’s a photo.
https://www.dropbox.com/s/qw8m5i6v7otkuer/leolego.jpg
It sits in one of my Dropbox folders. I can change it, I can delete it. I can do whatever with it. And, unless I do delete it, you can see it.
While I wouldn’t necessarily advise it, I’ve heard of people actually building small web sites this way.
Dropbox for devices
The machines need not all be PCs.
Of course there’s a Mac version available, but more interesting is that there are versions for Linux, as well as for iPhone, iPad, Android and Blackberry. One of the ways I use Dropbox is to keep a collection of documents1 (pdfs) on a variety of machines I might choose to use, like my phone.
On mobile devices, Dropbox will offer to automatically capture and upload any picture you take. That photo I shared above? I took the original with my phone. A minute or so after taking it, the photo appeared on my machine, automatically.
Dropbox security
Dropbox has been criticised for security issues.
I believe that the criticism is largely unwarranted, and as you’ve seen, I continue to use Dropbox daily.
The issue is that the files you place in Dropbox are uploaded to their servers unencrypted. That implies that Dropbox employees could access your files. Of greater concern is that the file could be turned over to government agencies with appropriate legal justification.
That’s true for any online provider that includes web based access, not just Dropbox. It’s true for your email, your social media, and your favorite photo-sharing site.
The problem is also easily solved when using Dropbox. At the cost of losing public and web access for the files you choose to protect, BoxCryptor Classic is a perfect solution.
Dropbox storage
Dropbox is free for up to 2 gigabytes of storage. That’s typically more than enough for sharing photos with family, documents with coworkers, or mp3 files with your phone. There are a variety of ways to “earn” additional free storage as well.
Additional storage is available for a subscription fee, should you need it.
Dropbox. I recommend it.
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A really great application – elegant and very useful. Working between laptop and work computers is so much better with Dropbox, I can’t believe how long I was using USBkeys and email for this purpose. Great suggestion.
Been using Drop Box for a few months and love it. Each time a file is changed, the change is updated on all your computers, and Drop Box lets you revert to previous versions of the file! This saved me big time a few weeks ago.
You mentioned that you were going to do more to eliminate spam on the comments to your articles. You might want to consider a flag button to report spam on comments. There is a spammer on this page selling some crappy solar watches.
11-Nov-2010
Funny thing, 3 months after I posted that comment, you hired Conny and me to check for spam.
I was invited by someone to sign up for dropbox but stopped when I saw I had to install their software on my machine.
Can you tell us more about what we’re being asked to install?
12-Nov-2010
Don’t worry about installing their program. It uses few resources and it’s necessary to keep the files synchronized. Drop box is my main data back-up for my most important files (not my only backup). I keep my home and portable computers synched. And I can get my files on any computer using their web site. I recommend and use Truecrypt to encrypt the ones I want to keep private.
also if you get your friends signed up to dropbox, they give you an extra .25 GB for each person signed up through the link you send them. You can get up to 8GB, the equivalent of a good sized usb stick.
and Leo, I appreciate the ability to directly post a comment on your page. You don’t know how many times I’ve given up posting on forums because of the complicated registration process.
To Mark’s point, I, too, bail out of most commenting opportunities for the same reason. Thanks, Leo.
And since writing that post, DropBox has doubled the free space to .5 GB per recommendation and up to 18GB total free storage.
I see on their website that it also keeps backups of the files on the Dropbox servers. This might be a plus or a minus, depending on your situation. (eg: confidential documents, though you probably shouldn’t use a service like this for anything that should remain confidential.)
Just thought I’d mention it, since Leo didn’t.
It definitely looks like something worth looking into. Thanks for the info.
So, if I understand correctly, the files I want DropBox to store must be in a specific DropBox folder on my computer, rather than in their normal MyDocuments folder. What happens if a system restore is needed on my machine? Are the files protected from change in the DropBox folder as much as they would be in MyDocuments or could a system restore delete the DropBox folder? Or am I totally missing the point?
17-Nov-2010
Leo, you consistently deprecate the use of Windows System Restore, but I don’t think that is warranted. Yes, a full system backup is superior to System Restore in that it will restore *everything* back the way it was before the backup, while System Restore restores only certain files and settings, plus it restores subsequently uninstalled programs and removes subsequently installed programs — but it doesn’t affect your personal files or documents. Well, I’m a belt+suspenders+skyhook type person, who has lost quite a few things before I started my failsafe system. So I not only do a full-system (or incremental-full-system) backup of my Windows 7 PC every single night, but I also create a System Restore Point — plus I run ERUNT (Emergency Recovery Utility for NT). That amounts to three different levels of security. The reasoning for this, which has served me very well over the past few years, is that there are times when a full-system restore from backup is too severe. For example, there may be certain programs, files, or documents that I don’t want to lose by doing a full system recovery from backup. In those cases a System Restore (running from Safe Mode) saves my day, and sometimes just an ERUNT recovery (again from Safe Mode) of just the system Registry is all that is needed to put things totally right. There is no need to use a flame thrower if a lighter or just a match will do the job.
The problem is that when things are really messed up System Restore can really fail the user. If people are using it instead of backing up then they can really be left hurting. So I’m sticking with Leo.
System Restore is fine when it works, but the danger ist that it can give a false sense of security and if it doesn’t work, you’ll wish you had a full system backup. If you have a full system backup, you won’t need System Restore. But if you chose to use both, then you’d have the advantage of a quick fix if your System Restore works.,
System Restore is awesome … when it works. The problem I have with it is that it seems completely unreliable. Too many people have reported to me situations – several situations – in which system restore simply and unexpectedly fails to restore anything. Try it and if it works, great. But never, ever, count on it.
As a fairly new user, I have installed Dropbox. It says to drag & drop a file into dropbox but doesn’t give instructions on how to drag & drop. Is it performed in windows explorer?
17-Nov-2010
LEO,
WHAT ARE THE MAIN DIFFERENCES BETWEEN “SHAREPOINT” AND “DROPBOX”? THANK YOU!
Another great tip, Leo. Many thanks. It works like a dream on our family computers.
I’ve been searching for a while for a tool to sync business related folders between my desktop and laptop. And I mean folders, not a newly created location into which I must first place any file[s] for syncing. I have what many would feel is a complex directory tree but, for me, it’s essential. Unfortunately, I don’t want to rely on saving and/or moving files into a new “Dropbox” folder.
Microsoft’s Sync Toy used to do the job and was excellent because of the permutations available, but for some strange reason has recently decided to refuse my instructions.
‘SugarSync’ is another utility like Drpbox available at http://www.sugarsync.com
I sent to you an invitation through its website to review the same here.
I love Dropbox have it on my pc’s and phone. So I can add the pictures from my phone to the pc’s very easily.
I was wondering if there is a way to keep the big files that I transfer between computers from going to the phone?
I did use dropbox but I deleted it when I got afraid that I might inadvertantly send personal details or files to friends. I became unsure how to just send them one file or photo and thought they might have access to all my documents. A description, step by step, of how to send would be helpful.
My kids touted me onto Dropbox several months ago; I find it very handy. For some reason my wife’s computer will not scan on our 3-in-1. I scan stuff on my machine, save it in Dropbox, and Presto it’s on her machine … and other computers where we might want to use it.
I love Dropbox and have been using it for about a year. However, I am concerned about the security of the files. For example, should copies of my tax returns be stored on Dropbox?
What is your recommendation for document security and the use of Dropbox?
06-Apr-2011
If you are concerned about which files your friends have access to , only files which have explicitly marked as shared or placed in your public folder can be shared with others. Here are the specific instructions on how to shar4e files with Dropbox:
Simply right click on the file in the public folder you want to send and click on dropbox -> copy public link. This will put the link in your clipboard. From there you can right click in an email and select “paste” and the link will be sent via email.
If you are concerned about sensitive files you could encrypt them using a program like Truecrypt.
http://ask-leo.com/truecrypt_free_open_source_industrial_strength_encryption.html
Putting sensitive data on Dropbox is risky unless you encrypt it first. A good free utility to do this is BoxCryptor
https://askleo.com/boxcryptor_secure_your_data_in_the_cloud/
I would certainly endorse the recommendations for Dropbox, and I also use a TrueCrypt volume for the more confidential stuff.
Two points you need to be aware of:
Dropbox won’t notice a TrueCrypt volume has been modified until it’s dismounted.
Even then, if, in TrueCrypt Settings > Preferences, you have checked “Preserve modification timestamp of file containers”, Dropbox will/may not notice the volume has been modified.
So it’s quite possible to get a “conflicted copy” of the TrueCrypt volume, which may be rather tiresome to sort out if there are many files in it, as well as taking time to up/download.
I have felt it necessary to write AutoHotkey scripts to minimize the risk of this happening.
Based on the remarks Leo made in Article C4540, I installed Dropbox on my laptop and put all my text files in there. DB gave me the 2 gig free storage I wanted to have off-site and kept the DB website file copies synced with the ones on my laptop so that whenever I added or changed a file, it also changed on the DB website. That part of DB seems fine, even though the software never actually told me, in words, that I was now backed up. I also wanted to share one particular subfolder and its documents with a friend who will have to implement directions in those files if something happens to me. Rather than continually giving him hard copy updates of those directions, I thought it would be easier to let him read them for himself. I was curious as to how sharing might work, so I “shared” a folder with myself, using a second email address I have. That’s when I learned that the email that is generated to the invited person immediately asks the invitee to download Dropbox onto his own computer. It simply tells him that he can’t see the shared files without doing this. If I were that invited person, even if I had been given a little prior warning from my friend, I would be leery of downloading. I also learned that the person or persons you share the folder with have the ability to change your files. I didn’t want to collaborate with my friend on files, but just give him access to looking at them. DB also said that the person you invite to share the folder could invite others to come see the documents in that folder as well. At this point I backed out. I don’t want anybody changing my files nor inviting unknown persons to look at them, either. DB says it is working on this, but it isn’t clear whether they have perfected it yet. I backed out of the shared folder with myself as quickly as I could. I took the sub-folder out of my Dropbox to do that, but I noticed that the folder and its files still retained the little green circle that tells you the files are still “syncing” and backed up by DB, even when I rebooted to give it time to “take.” I consider that a glitch. When I put the sub-folder back into DB, but not in the shared folder, I knew only I could access it. Somewhere in the DB help questions and answers I read that there is a way that a person you share with does not have to download Dropbox but can go on the DB website somehow and see the shared files. I have never been able to find this comment again, so I don’t know whether it’s possible or not. When I asked one of DB’s tech. support people, I did not get the direct kind of answer that I needed. Leo’s article made it sound all so simple, but the kind of concerns I’m facing were never brought up. DB’s Q & A way of giving information is scattered in many different parts of its website rather than one topic being all in one place, yet I’m never sure that I’ve hit all the places!
Leo posted my concerns about DropBox. A computer guru friend of mine began reading about it for me and discovered a comment someone sent in saying they had such a hard time downloading DB that they signed up for Syncplicity.com instead. I decided to try that syncing website myself. I discovered two interesting things: both DB and Syncplicity are home based in San Francisco. The functions of their sites are so completely similar that I decided that maybe some tech employees of DB must have left DB to start an improved site. I found it better in many ways and am glad I went with Syncplicity instead, even though I’ve never been a fan of companies that copycat what other companies do.
I have been using Dropbox for about a year and have been very happy with it. I use it to work on files from my work PC to my personal laptop. I haven’t had any problems until just a couple of weeks ago. I worked on 3 documents all located in one particular folder inside of Dropbox on my laptop, all on the same day. For those three docs only, I cannot get them to come over to the file on my PC. The document is there, on my PC, it says that it has a certain amount of KB’s, and when I open it, it shows there are words, and then the word count goes to 0. It almost acts like all the text is hidden. I’ve tried everything to find where I could disable it, and have disabled everything that could make it have hidden text, but it happens everytime. There is a fourth document in that folder, which is an Excel doc (the others are Word) and part of what I worked on that day also does not show up, but the rest of it is fine. I can go back to the document on my laptop and bring it up, and put it back into Dropbox, but I still can’t see it on my PC. Do you have any ideas? Thank you!
For DropBox, which I finally have added to most of my many machines, I recommend NOT working directly on documents in the DB folder. Rather, copy (not move) to another folder. Work from that copy. When you have completed work, copy (not move) back the new, edited, finished document to the DB folder, with the same name, thus overwriting the previous version. Or, if you want both versions, make sure you used a new file name or appended a version number to the name. I believe that this might solve the problem of files that get messed up because of multiple versions in the folder.
06-Dec-2011
An ‘applicaton’ that requires installation of it’s software in order to see images at it’s website — WHEN NO OTHER PHOTO SHARING SITE DOES – has to be suspect.
Sorry, but I have enough “JUNK” on my computer as it is.
09-Dec-2011
I had not appreciated the ability to synchronise between remote computers using Dropbox which really is a most worthwhile feature.
I have been using Windows Live Mesh for this purpose and wonder if anyone has made a comparison between the two and would like to share their experience?
have been using dropbox for several years.
it is EXCELLENT.
it works well and is reliable
cAUTION to anyone posting some sensitive file they would not want others to see (financial, etc)
encrypt it first before putting into dropbox.
OR, use truecrypt vault.
NEW FEATURE –
auto-upload of camera pictures; plug camera into computer, and auto-play comes up, and an option exists there to automatically load files into dropbox; it loads the files locally and to the dropbox cloud.
GREAT for backup of files on a vacation, etc.
COMMON SENSE prevails with use of such a product regarding security, sensitivity of files, etc. BUT, the software and the company seem very reliable.
nick
ADrive.com gives you 50GB free storage.
Box.com gives you 50GB free storage if you sign in before March 31, 2012 and it ties nicely to your mobile devices.
Dropbox share file link is very long and difficult to type (when one cc to a paper doc). Is there a way to make the share link shorter?
@Randy
There are several URL shortening services that work really well for that. One is https://bitly.com/
So drop box is like evernote in that it syncs all your notes? So why not just use evernote?
@Ellie
DropBox automatically syncs files between computers. These can be photos, songs, movies, programs or anything which can be stored in a a file. When files are placed in a DropBox folder on your computer, they automatically appear in the DropBox on the other computer which is associated with that DropBox account. Evernote works a little differently, as you have to go through the Evernote program to upload or download files.
I bought a business upgrade. It’s been great, with some caveats. I work with big computer models. I drop the model in the dropbox and it’s available for others to work with. Be careful about writing the results back to the dropbox – make sure the original dropped file is closed or you will have write conflicts that dropbox attempts to resolve in a way that I’ve never fully understood. Also, if you share enough data to a folder that non-upgraded users have access to, it can take their accounts over the free limit, causing serious sync problems. Another issue, that I have, is the amount of data transferred on my limited rural internet data account. Syncing the machines causes the same data to flow from Dropbox’s server to each of my machines, unless I tick a button for local LAN sync, but I actually have no way to know if it’s working. But, I still applaud this product. As executor of an estate, I was able to share all of the ongoing documentation with the heirs by setting them up with links to a Dropbox folder, achieving transparency for all.
I wanted to mention that Dropbox, will start and run as soon as you power on your computer, so if you have an older computer with limited CPU you could notice it running slightly slower with Dropbox installed. Probably not an issue for most people. Regarding the security issue, if that is a concern then don’t use Dropbox for those files that you are concerned about. There are many benign uses for Dropbox where security shouldn’t be an issue.
Thanks for this interesting article. Why do you recommend DB rather than Google Drive, whose applications are about the same?
J-M
Either will work well. Dropbox is perhaps the earliest, and most ubiquitous, and the one with which I have the most experience. (There are a few features that I don’t think Google Drive has, like file history.)
Have you considered using BitTorrent Sync (http://www.getsync.com/platforms/desktop) rather than DropBox? BiitTorrent Sync does not require that the data be stored in the cloud. Also, data is encrypted before it leaves the computer and is not decrypted until it reaches its destination. Because the encryption key is stored only on the sharing computers there is no chance that the data can be intercepted and viewed. Like the original BitTorrent, the more computers you have sharing the data, the more efficient the updates. Shared files are also segmented so that if a part of a file changes, only the changed parts need to be retransmitted.
I use BitTorrent Sync heavily here at home. I *love* that I can get, essentially, unlimited cloud storage by using the linux version on my servers. It’s not for everyone, but it works well.
After I registered on DB I got an email saying that I had recommended someone to share my account; their email address was unkown to me. I checked my registration and found that the second I registered the invitation to share was logged (without me doing anything). After going around with DB security they finally claimed that this person had gotten my email address and was lurking at DB for me to register. Sounds rather strange and raises doubts about their security although they claimed that nobody could share my files with my permition.
Do you know how Dropbox compares with the Onedrive App for Windows? Although you cannot upload folders directly to Onedrive, apparently you can with the App; and as I have 25 Gb free on Onedrive, compared with 2 Gb on Dropbox, would you agree that Onedrive looks like a better option for backups?
In my experience, they both work well. DropBox has a few features I like, but if OneDrive gives you more storage, I’d go with that one. I personally sprung for the paid DropBox. But that’s just because I wanted a complete backup of everything.
I have been using DROPBOX for a couple of years and absolutely LOVE it. I installed it on my husband’s computer [in the next room] and on my Aunt’s machine [the other side of the world] and find it so incredibly useful in both instances. Don’t know how I lived without it!!!
Thanks for a great website Leo – you are the best!!!
I love Dropbox and use it to share with friends. However, I agree with the previous mention: I also don’t want to rely on saving and/or moving files into a single Dropbox Folder. SugarSync is my program of choice since it allows me to maintain my Windows Tree Structure and, instead of placing moving folders to a single Dropbox folder, I simply select the folders I wish to copy to the cloud. The selected folders are synced to the SugarSync Cloud. A free trial is available at: http://www.sugarsync.com
I signed up for Drop Box when I first heard about it a few years ago. I am sure it is as many say, a very useful tool, and helps many people in many ways. Personally, I found it to be too “bossy” for my liking.
By that I mean it automatically saves just about everything that comes into your computer from many sources, and that I didn’t like. Perhaps I am just not using it correctly or have some settings wrong, but I stopped using it just because it seemed like it was a “Grab and Run” program, and soon ran out of space and wanted cash for more. Also, our IT department at work forbade us from using it for anything remotely related to our work. And I am sure they are much wiser than I am about this kind of stuff.
I use dropbox too but its implementation in my life is a bit different.
My relatives have really poor computer skills and I generally helped them using remote software like teamviewer. Most of the time it involved updating an excel file which contained bank details or bank statements. This needed me to call them, get a user-id password combo and then update the file when both of us needed to be free and available. Using dropbox eliminated the problem bypassing almost everything.
However, I too used dropbox which had files which I did not want to share with the world or say anyone but just only between me and my devices which posed a big problem.
Well, I created a different user account for them in Windows. Dropbox synced their files when I logged in to their windows user account and mine when I used my user account. This is the setup that I have been using continuously for more than two years without any glitches.
Ravi.
Is there any difference between Dropbox and Google – My drive. I’ve been using Google for years with no problems and it offers much more memory. Also allows file access to my phone.
There are a few small differences, mostly in sharing capabilities (I prefer DropBox for that). Dropbox also allows you to upload files via their web interface. Otherwise, for synchronizing files and folders, there’s no real difference. If you do find a feature you like in one, you can always have both installed on your machine. I used to use DropBox together with OneDrive to have all of my data backed up on the cloud. DropBox made me an offer I couldn’t refuse ($70 a year) and I got the paid version of DropBox and I threw all of my user files into the DropBox folder and now I don’t have to remember which folder I put my files.
Dropbox can be installed on your phone (iPhone, Android and I’m sure Windows Phone as well). They are very similar. I don’t think Google has the file history feature that DropBox does.
Hi Leo, you have recommended Dropbox, it’s attributes and how useful it is but is OneDrive so poor that there is no mention of it? There is 30Gig free storage and I have found it works well, shares easily with my family & friends and syncs and updates to my other computers, android and phone. Should I also be using Dropbox instead; are there hidden dangers with OneDrive? Thanks very much for all your interesting comments and advice which I thoroughly enjoy!
dropbox saved my bacon last year when my laptop was stolen. All my active client files were in Dropbox. I bought a new laptop about 90 minutes after I was robbed and was able to download all my stuff from the Dropbox site. I bought the upgrade for $99 per year and it’s so worth it. I haven’t tried it yet on my phone though. I do use it with several clients, it’s easier for them to send me photos, etc. on Dropbox..
regarding dropbox, I have been taking a class using e-mail to communicate , now I need to replace my computer but I am having no luck putting the e-mail into the dropbox. I have been using yahoo mail. any suggestions? thank you.
Yahoo mail is web mail, so I’m not sure why you want to put it into dropbox to begin with? Or are you using some kind of email program to access your Yahoo! mail?
My friendand I both have dropbox and have been able to share files untilrecently. Now my dropbox says it can’t find her and hers says it can’t find me. How do I fix this?
I have Dropbox on all of my PC’s to support another application that uses it for data sharing. I find that Dropbox is a high memory user (120MB on Win7) when it apparently is doing nothing. Since this machine only has 6GB memory, the BIG Three applications (Firefox[not good at releasing memory], Outlook[what can you say?!], and Dropbox) together can use a gig of memory.
So, why is Dropbox using so much memory when it really isn’t doing anything?
Dropbox will be constantly syncing, and perhaps that is using so much memory. Try changing it so that it’s not syncing and see if that reduces it’s memory use. Do know that you’ll need to turn syncing on again every time you need to sync the folders.
Thanks Connie! Guess we’ll have to live with the syncing… shouldn’t be a problem on new 16GB machine…
Dropbox sounds very interesting and your article today has convinced me to try it. Couple questions:
1.) I use Windows 7 and locally installed Outlook. All my email, contacts, calendar, tasks, etc. are stored locally in a .PST file. I don’t often reboot, and Outlook is running (the the PST file is therefore open) virtually 24 hours per day and being updated almost every time an automatic send/receive executes, which is every 5 minutes . If I move my PST file to the Dropbox folder (and reconfigure Outlook to access it there), will it sync properly and reliably to the Dropbox server, and to my other devices (laptop and several other Windows desktops)?
2.) Are there certain types of data storage, like databases such as Quickbooks, or music files stored in iTunes, etc., which do not work well (or at all) with Dropbox?
1. It should, but if you use Outlook to synchronize your email programs with the server, it would accomplish the same thing and save you space on Dropbox if you are not using the paid version.
2. They should work with Dropbox, but again, iTunes is already a cloud sync service.
I would not place my PST file in a sync’d folder – dropbox or any others. Same for Quickbooks or large(ish) “database” files, especially those that are under constant access. Instead I’d copy them there periodically instead. In theory they should work, but I don’t know how frequently, or how reliably, they would be synchronized.