If i owned that system, i would install win 2k.., DX9, and some older vid card drivers.. (my old system has an ATI card, which seems to run everything i own)
Running win 2k, you should have no problem with anything from 95-2005 outside of some very rare instances. For me the only thing it would not run would be a very old Rouge squadron disk, that will only run under win 95. Awesome game, and first starwars game i ever played that you used a snowspeeder and a grappling hook and took down At-at's! It had it all. ground game fighting troopers, space in ships including a yt-1300, and much more.
Darn..I really need to get a new (old 8 gig HD) to get my old P1 266 back running.. the mother board maxes out about there, besides win 95 only has 2 gig partitions anyway. then install the dreaded win 95! But hey it has 100 megs of ram, and a 16 meg vid card.. So it rocked Rouge squadron!!
so yea, i hear ya on extra boxes.. but isn't it so nice that the monitors for 3 systems take up so much less space these days? 