ive got an opinion, dont upgrade at all to windows 2000. i tried it, and it just doesnt work for audio recording. it works fine with cakewalk but... i head some problems with the cakewalk setup but it was easily fixed (even though i dont remember now what the problem was or how i fixed it), i think it had something to do with the direct x in the installation. the only other problem i had with using cakewalk in it was a few graphic problems, very minor but can get annoying.
i really dont recommend windows 2000 for anything yet but server administration (maybe a few other things). believe me though, with audio recording, youll wish you wouldnt have upgraded. i recommend upgrading to Windows ME. helped me out alot (i think its the reason why i can now playback 128 tracks with a pII 333 system). please, when you do upgrade, let me know if you can playback that many tracks after too so i know if that was the thing that did it (so i dont have to worry about losing this if i format my harddrive).