I just wrote up a bunch of notes on the Chandler wiki about remote debugging with Wing (the Python IDE), having just finished a session where I fixed a problem that only occurred on an automated-build machine hundreds of miles from here (with two firewalls between me and it).

The Wing docs treat remote debugging as an “advanced topic”, but it really works well once you get over the setup hurdles. Even if you’re just doing remote debugging from a different machine on your desk, it’s a real boon when working on UI code to not have your debugger’s mouse and keyboard interfering with the target’s mouse and keyboard… so give it a try.