I use a Sidewinder Precision Pro USB with Windows 98 and a Voodoo 5.
I haven't tried it with Win2k, but if it sets up and calibrates in Windows, it should work in the game. However the one area where I expect problems in Win2k is with controllers, so I would not be surprised if there were some issues there.
Can you test and configure this thing in Win2k? Have you hit MS's web site and got the latest Sidwinder software?
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Lephturn - Chief Trainer
A member of The Flying Pigs
http://www.flyingpigs.com 
"My P-47 is a pretty good ship, she took a round coming 'cross the Channel last trip.
Just thinking 'bout my baby and lettin' her rip, always got me through so far."
- Steve Earl