Instead of a hard reset, can you press 'command' 'q' to force CrossOver Games to exit? If you still don't recover the Mac, can you set up both systems in windowed mode to see if you can use your activity monitor to kill and processes?
First, start your Activity Monitor (or at least set it to stay in the dock). Then, go to 'Configure' and choose 'Manage Bottles'; select the Red Alert 2 bottle and launch 'winecfg' from the 'Control Panel'. Choose the 'Graphics' tab and select 'Emulate a virtual desktop' and set the 'Desktop size' for something smaller than you screen size (basically, so you can see your dock while Red Alert 2 is running).
Now, when you exit out and get the crash, try to quit CrossOver Games with 'command' 'q'. If that does not help, try accessing the 'Activity Monitor' to see what is 'not responding'. Then, try to highlight and quit the process(es) in question.
If you are able to find a specific process that is not cleanly exiting it could be that CrossOver Games is not listening in the right place. You should consider opening a support ticket or sending an email to info@codeweavers.com with this information. While C&C: Red Alert 2 is not supported, it would be an interesting bit of information for our developers.
Congrats on getting it to work and many thanks to those that helped!