Was surprised by this so just did a little research. It appears (https://stackoverflow.com/questions/18578439/using-requests-... , http://docs.python-requests.org/en/latest/community/faq/#wha...) that this is fixable in python 2.7 so not a show stopper, more of just a good to know.

Note that many people don't use requests, which has a rather large dependency chain, and sometimes you don't have much choice. e.g., feedparser doesn't use requests, nor is it likely to because of the dependencies. PEP 466 https://www.python.org/dev/peps/pep-0466 has more information, too.

Are you unable to throw any number of the faster, event-driven webservers/reverse proxies in front of Python 2.7 to satisfy your SNI needs?

I am "able" to do lots of things, but running a reverse proxy just so a command line script works is outside the bounds of "willing".