This is likely to be even less help
I've used XP Pro for a couple of years now (at least it seems like it) and it allows you to create separate logon IDs for as many users as you need. That way I have the ability to run independant instances of outlook for each user and neither XP nor Outlook seem to complain about any licence issues even when two or more users are logged on at the same time (but only one active user, obviously). I keep my diary, along with an iPaq via Active Sync, as a discrete entity. It doesn't affect anyone else's Outlook data nor do they affect my iPaq.
This is because of the way that each logon has it's own user profile and directory structure. Don't know too much about Win2k but if you can create separate user login IDs that might be a solution.
Over to the experts .....
Good luck
ST