Stolk, I think you are still missing the point entirely. This is gaming software, a port of a arcade game for the N64 released years ago. It is NO longer in development and hasn't been for quite some time. Game companies don't continually upgrade and support their game products forever. If a game is successful enough and the demand big enough then they will make sequels or maybe expansion packs. But the original product doesn't get upgraded or patched to run just like the latest and greatest.
In the software company I work for, our clients are medium to large firms that continually pay maintenance fees to support our product line of financial accounting systems, allowing us to keep upgrading it and patching it to run on latest OS. RS may still be available to buy at discount prices, but I bet the sales and revenue are modest and not enough to warrant new upgrades. Ask Lucas Arts, see what they say.
Our only hope for playing RS in the long term future is a sequel developed to run on latest platforms. This may be happening since there was a RS demo for the GameCube so it might in the works as we speak, no official word yet. This could lead to another port to PC which I bet will run on WinY2K and WinME and have multiplayer. We'll just have to wait and see what happens.
Did you ever get a official response from Lucas Arts technical support regarding RS compatibility with WinY2K?
Ties are flies, swat'em!