I have a few old crunchers still running win2k. I recently did a successful windows update on one of them. It had been a while since last update but it didn't need a massive amount of new updates. Then I tried updating a second win2k comp and it did NOT work. For that comp the time since last update was much longer.
What I'm saying is, you might not be able to get up to speed on windows updates from a fresh install of win2k any more. From what I could see microsoft apparently only provides limited updates for them at this point.
So you could re-install it but it could happen that you can't update it at all.
Anyone here recently done a fresh install of win2k? Does it update?
Try this in WinXP: right-click on the application icon/file and choose properties. Then select the Compatibility tab. There you'll see a drop-down box with different versions of Windows. Select Windows 2000 in that. There are a few other compatibility options there too like disabling XP themes. I don't know if that will make your win2k specific apps work correctly, but worth a try.