Other than it's the best OS Microsoft has produced to date? No.
It used to be that the Win2k drivers sucked for things like video cards, but that has changed. AH works fine with Win2k, and the only holdups are normally joystick support for things like the control program you mention.
I would do three things.
1. Download Win2k drivers for important things like video and sound before you start so you have them on hand.
2. Do a clean install. Upgrades only inherit all your problems from the old OS. Trust me on this. While the Win2k upgrade program works surprisingly well, in my experience most folks end up wiping and doing a clean install of 2k anyway after they experience problems with the upgraded version. The clean install version works fantastic.
3. Once it's set up, use windows update (look on your start menu) to get SP2 and all the other patches. Use Windows Update on a regular basis to stay patched and secure.
Oh, and be sure to use NTFS file system as long as you are not dual booting.
