I upgraded from Windows 98 to Windows XP, and I just took the hard drives from my old computer and installed them as slaves in my new computer. Almost all my programs ran fine, including some dating from my DOS days. (In fact, DOS programs run much better under XP than they do under 98.) I've upgraded this way for 15 years - just transferred entire hard drives from machine to machine - so I have Win3.x, Win95 programs, Win98 programs, and DOS programs, all mixed together. The upgrade to XP was the easiest ever. I did have to set some programs to run in "compatibility" mode, but other than that, all was smooth and sweatless.

There were only two programs I couldn't get to run. One was my Day-Timer software, which has been discontinued and is now unsupported. Actually, it runs, but gives me an annoying error message every time I start it. I can live with that, though. The other program that wouldn't run was an HTML editor that dated from when Win95 was new. There had been four upgrades since, the oldest three now being offered free. I installed one of them, and that fixed that.

I do run XP in "classic" mode, though. I just can't get used to the standard XP look.