Transferring old system to new computer

I have an old version of CUBASE VST with Wavelab 3.0 on an old Windows 98 desktop pc. I haven’t used it for a quite some time but now have time again to do some recording so I would like to get a new system that I can transfer the program to and then install the old drive as a secondary drive so I can also open the old files that are saved on it. I was actually thinking of switching to an Apple computer too. Does anyone know if any of this can be done?
Or, if not, …if I bought a new Apple computer and new software would the new system recognize any of the old files?

If you’re lucky you can run Windows XP as a second OS and maybe get Wavelab 3 running, not sure about Cubase VST. Wavelab wasn’t available for Mac those days, so that won’t work. No idea how far legacy OS can be run in a virtual machine and the like.

No idea if Cubase VST projects could be opened with SX1/2/3 (never used C VST myself). And if it does, those old Cubase versions may work with XP but not with anything younger. Honestly, if you have time to make music, don’t waste it with troubleshooting the weird interactions of soft-/hardware generations that you can expect.

I’d probably just use this old computer and try to bounce/export the files you need as wavs/midi, then import all that stuff into a current version on a current machine.

I brought an old computer up through Win95->Win98->XP and at each step is was a hair-pulling experience to bring at least a few of the old programs forward, although others worked fine.

If you have a patient friend with a fairly new computer and an external usb to IDE docking station, you can try running some of those old .exe files directly from their file locations on your old hard drives without going through a formal installation procedure which would require having original installation discs. Just double click on the .exe files in File Explorer. You may get some to work, I don’t know if Cubase stuff would be among those, however. That definitely won’t work with any Mac or Linux system, even with Windows emulators. You can pick up relatively recent early generation i7 and i5 computers with legitimate Windows 7 or later installations for less than $200, Amazon has some refurbs. That’s what I would do in a budget conscious situation, assuming the old exe files prove able to run on such machines.

In any case, don’t put a Win98 or XP computer online, they are sitting ducks for hackers. Vista is almost as bad.