"I recently had an e-mail from a Windows developer in the Ruby community who pointed out how opaque many Ruby projects are regarding Windows."
I guess my response to that would be that Microsoft is quite opaque regarding Ruby. By being such a closed system, Windows doesn't do anything to help developers improve Ruby library compatibility.
Compare this to Apple. Apple builds Ruby into its operating system, contributes patches upstream, and is even supporting the development of MacRuby, which more tightly integrates Ruby into the Mac OS X operating system.
So the opaqueness goes both ways in my opinion.
Due to this, I am very impressed that Ruby even has the level of support in Windows that it currently enjoys. I would say that Windows hackers should keep up the good work and submit substantive patches as often as possible.