Hmm. I'm not sure what bothered you about cygwin, but if it has been awhile it's worth another look. For me it makes windows tolerable, and even productive.
I'm scared more by your thoughts of transitioning from OS-X to windows. I've seen a bit of OS-X and am slowly be warmed up to it as an option for my next machine by some folks here. What is causing you problems with it ( enough to swtich to windows-wow.)? -- http://mail.python.org/mailman/listinfo/python-list
