I had a lot of problems with Win98 on the laptop, but since I installed Nortons Utilities it's been much better.
With Windows ME and 2000, there are websites around that will give you a guide on what games will and won't run in that environment, or what you need to do to get some games running. I've got TOCA2 running under Windows 2000 after a couple of little changes to the .ini file.