Unfortunately, you’re not going to get the scenario that you’ve described working. You’re going to have to actually reboot into Windows 98. You might be able to do that off of an external drive if you’ve got Windows 98 completely installed on that drive, as well as the program. I don’t think you even have to move your backups for it to work.
But before you go down that road, I want you to investigate a different solution.
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This is a job for….
In my opinion, this is a job for a virtual machine. This is a solution I use, in fact I rely on, that I think will make your life a whole lot easier.
Like you, people often consider installing Windows 98, or some other older operating system that they still need, on a second drive. It can be an external or an internal drive; it could be a USB flash drive or a USB external drive.
You can set up some kind of dual boot situation so that when you boot your machine, you choose which operating system you want to boot into. To me, that’s just too much hassle. Half the time I’ve been in those kind of situations, there’s something that I’m doing on this operating system that darn it, I wish I had the other one up to do.
Virtual machines provide a solution for that. They’re basically software that emulates a machine within your machine. It’s really hard to describe the technology, so I’ll just describe the results.
Here’s the scenario after everything is set up: You have one operating system that you would boot your machine into. That’s probably Windows 7 in your case. After that’s up and running, you would run a program called a virtual machine manager. In that program, you will double-click on a virtual machine representation that has been configured to run Windows 98. Now, here’s the key part: a window then pops up that looks and acts as if it were its own separate computer – completely.
It’s a virtual computer. A virtual machine.
Within that window, you’ll probably see a virtual BIOS run for a couple of seconds, which then loads Windows 98 exactly as if it were a machine running Windows 98. After a few seconds, you are in fact running Windows 98 in a window within Windows 7. Then of course, you can fire up whatever old program it is you need to run in Windows 98.
Virtual machines can be moved; they can be cloned; they can be copied very easily. The tricky part, of course, is getting one set up. You would need your Windows 98 installation media, because to start all this, you’ll be setting up Windows 98 from scratch, just like you did when Windows 98 was current.
This time, you’ll be doing it within that virtual machine window.
I use Virtual Box by Oracle for my virtual machines. In fact, like I said earlier, I rely heavily on it. It’s how I run Windows XP on my Mac. It’s how I run XP, Vista, 7 and 8 all on my Windows 8.1 desktop machine.