Okay, so after a lot of help from @jballanc
on the #macruby
IRC client, we determined that this is a Mountain Lion-specific problem caused by some changes to the way CoreGraphics is packaged in the latest XCode. Here's how to solve it if you're running into it:
Regenerate your Bridge Support files for both CoreGraphics and ApplicationServices, using something like:
gen_bridge_metadata --64-bit -f /System/Library/Frameworks/CoreGraphics.framework/ -o /System/Library/Frameworks/CoreGraphics.framework/Resources/BridgeSupport/CoreGraphics.bridgesupport
In Mountain Lion, you will need to explicitly load the CoreGraphics framework from your MacRuby code -- but in versions previous to Mountain Lion, doing so will crash. So you'll need something like the following check:
framework 'CoreGraphics' if (/12/ =~ `uname -r`) == 0
Depending on your environment, you may or may not need to explicitly link against ApplicationServices.framework in your XCode project settings.
Doing all of the above allowed me and my Snow Leopard-using partner to share the same code base and have it work for both of us.