It's unfortunate that there really isn't a solution that solves everything, it's always been a problem with PC gaming though. The best thing to do is just build an older PC for yourself and install Windows 95 and/or 98. Then in some years you're gonna want a Windows XP system in addition (probably).. If you want even older games Windows 95 might not even work that well.
Personally I find that to be more trouble than it's really worth.
For older PC games I try either a Virtual PC (using windows 98 of course) or Dosbox. But I always search for workarounds for modern OS systems first, or just try it for myself if I find nothing. For instance I'm currently on the RC build of Windows 7 and playing the Thief games flawlessly, which seems odd because those games are notoriously incompatible with versions of Windows after 98 and require a lot of workarounds. But all I did was install the games and the codec for the movies, and they worked great. I added in a modern resolution patch to run them at 1680x1050 as well, really nice stuff.