I doubt you'll simply be able to install it and play, Win 95 to Win 7 just seems like too big of a gap. Though there's no real reason not to just try it and see what happens. If it doesn't work, you can always try running in Win 95 compatibility mode (right click program, go to properties, and set it to Win 95 in the compatibility tab). If that doesn't work you could always try to find a Windows 95 emulator that runs in Windows 7, but that can take some work to set up, and some games just don't work well on an emulated OS. As far as the stick goes, Descent 2 is probably not programmed to recognize a USB joystick, so it probably won't work, but it's at least worth trying. Again, you could always try to find an emulator that will take your USB joystick input and convert it to something Descent 2 will recognize, but that'll take some searching on your part to find.