I'm using a Win2000 bottle.
I was able to get it installed fine and replace the Sims.exe file with the cracked CD Sims.exe file.
After this point when I tried to launch the game, it starts to boot, you can hear the music and you can see the titlebar. It stays up for a few seconds before just crashing.
I found this reddit post:
https://www.reddit.com/r/thesims/comments/o8ksv0/sims_1_and_windows_10_set_locale_returned_null/
It says to us this widescreen hack (https://github.com/FaithBeam/Sims-1-Complete-Collection-Widescreen-Patcher/releases), then run the game with the -w -r1902x1080 command. So in CrossOver, hit the "Run Command" button in the top right, navigate to your Sims.exe file in the game folder, hit "Open", then add the -w -r1902x1080 command to the end of that path.
It should look like this: "/Users/MyName/Library/Application Support/CrossOver/Bottles/Windows 2000/drive_c/Program Files/Maxis/The Sims/Sims.exe" -w -r1902x1080
Be sure to select "Save Command as Launcher" so it creates a new icon for you in CrossOver.
Now at this point when we try to launch the game we have a new error that says: "Game cannot be started because: Color must be set to 16 bit (high). Exit Now.
I'm not sure how to resolve this issue just yet..