I used to dual boot win98 and nt4, I have run win2k now since it came out and no longer need to dual boot. The only game that wont work on my system so far is Mechawarrior 2 (my son wanted to play it.)and I can live with that. Unreal Tounament,Quake2&3(haven't tried Q1 yet), Deus Ex,Thief2, and all my other older games (no sound in Duke3D🙁 though)play great. I'm not so sure about DX8 though. I'm using Dx7 with no problems (I dont have hitman however). You should have far fewer problems setting up win2k, thats my experience anyway. Gaming OS...most definately IMHO! I haven't heard many good things about WinMe.