Hi Matt,
Thanks for your bottle_ssl.py. Seems to work fine. Based on my experience with the technique you started from, Python's SimpleHTTPServer didn't have threading, and when Chrome accesses a server via SSL, it needs at least two threads (Firefox doesn't), so to get SimpleHTTPServer going, required two patches.
However, once I applied your patch to bottle, I was surprised Chrome also worked with it... until I discovered that wsgi-multithread was True, so the wsgi code must already implement multithreading, even though in the DEPLOYMENT section of the bottle docs it mentions only being a single threaded server... maybe wsgi wasn't threaded when that was written but is now? I don't know the history.
Anyway, it is working great, some 5 years after you wrote your patch.