about running DOS programs in 2000:
2000 doesn't have any built in sound blaster emulation. There are third party programs that claim to add it, but my experience with them has been not good.
there was also something about the interrupt flag. one of those programs came with a utility to replace something with nops. I forget the details. I think it had to do with NTVDM not remembering to restore the interrupt flag.
I tried using the DOS version of heretic to play a network game over IPX, but it wouldn't work (although I can play DOS Warcraft 1 over IPX, but with no sound). DOS games seem to freeze up if I switch away from them and switch back.
I've been using wheretic, but it seems sluggish at times, and it seems to have a bug with the sound effects (specifically, sound effects keep playing even after the monsters are dead).
With regard to upgrading:
I've almost always preferred regular installs to upgrading. I guess I just perceive it to be cleaner.
Going off topic:
I think the trend toward recovery partitions instead of installation CDs is not good. On the plus: you don't have a CD to lose, and it makes wiping computers more convenient. On the negative: Lose the HDD, lose the recovery partition. Also, what prevents a rootkit from corrupting the recovery partition?
I've gotten a deal with a local pawn shop. They pay me a reasonable amount to wipe numerous computers, mostly Vista and Windows 7 laptops. I don't have any Vista or 7 DVDs, so I rely on the recovery partitions. For XP, I can use a Dell XP Pro CD I bought on Ebay.
In my life, I've installed (at least once): Windows 95b, Windows NT 4, OS/2 Warp 3, FreeBSD, etc.
I've installed numerous times: Windows 98SE, 2000, XP, Vista, 7. I've also configured numerous DOS boot disks. I don't know if that counts as "installing".
My favorite OS to install and use is XP.
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