I had a working win2000 bottle back in CXG 8.1.4. However I should note that I owned the steam version of the game.
It had a weird quirk where upon launching the game it would try and install directx every single time you launched it. The movies failed to play properly in 8.1.4 but they had been working fine in 8.0. (In fact I would rate the compatibility as gold in 8.0).
I no longer have that bottle for current testing. However hearing that this game no longer works I tried a few things.
I first installed it onto my current steam bottle and gave it a go. This bottle has had a lot of things go through it, so I consider it "dirty". Trying to launch SOTS through steam just has it exit. With no errors or anything.
I then tried to recreate my win2000 bottle from before. Upon launching SOTS it tries to install dxredist, .Net 2.0 and vcredist.
It appears to install the first two fine and then it errors out on the 3rd one. Rebooting the bottle I try to launch it again. This time I get a c runtime error and the game won't launch.
Putting on my thinking hat, I scrap the win2000 bottle and start fresh with a winxp bottle. Before I install steam I manually install .Net 2.0 and vcredist 2005 from crossovers install menu. Then I install steam and SOTS.
Launching SOTS gave a few surprises. After trying to install dxredist yet again, it attempts to install .Net 2.0. Since its already installed it gives you the repair or remove options. I click cancel and then it tries to install vcredist as well, which crashes and fails.
Rebooting the winxp bottle I try launching again, this time giving me the c runtime error.
Now I have two bottles with SOTS installed with steam, one giving me a c runtime error whenever I launch it and another bottle which gives me no indication of what is wrong and just exiting immediately. Neither working.
I know this game used to work flawlessly in a win2000 bottle but I just can't recreate it so I have to agree that a regression has happened.