Here's a status report as of Feb 26:

With Bill's wrappers, I can get remote debugging to work, but local
debugging still freezes because of thread issues in windows. I am
growing very tired very fast with that operating system and would
definately appreciate any help getting Mr. Guid to play nicely with it.
Until then however, I cannot spend too much time concerning myself with
the issue. For all the windows users who wish to use Mr. Guid, I am
sorry. My only recommendation right now is to get ruby running in
cygwin. I will probably tinker with that and post my results and or
HOWTO's.

Sorry for all the inconvenience.