I just used Wineskin Winery again to play another favorite of late 90's / early 2000's: Championship Manager 3. This time running "natively" on macOS Catalina thanks to wine!
I'm looking forward to porting more of my old games from my Windows 2000 VM to my mac. I just ported CM3 and and also got Counter-Strike 1.6 as well as GTR Evolution (RACE07) working, the last two came from a Steam app for windows I ported too.
I only failed with rFactor 2 - I can get to the game launcher, but it crashes when I try to run the game from there. I bet I can get rFactor 1 working.
Next on my list should definitely be Flight Simulator 98. I could try 2000 or 2004, but I don't remember playing them (maybe 2000, I remember having the box).
And I've also got Grand Prix 4 working (and faster than my Windows 7 VM!!!!), but only in its "pure" condition. I also want to play the mods of past F1 seasons I have, but the editors for the game aren't working thanks to stupid Apple and its notarization of apps. I've left it to the VM for now. This can be the end of gaming on virtual machines for me! yay.
"Design isn't just what it looks like and feels like. Design is how it works."
JOBS, Steve.
READ: Right to Repair sucks and is illegal!