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“2.7.11” is the Python version, the interpreter that is running the scripts.

07:10:48 PlexConnect: Version: 0.5-dev

This line is the actual “version information” of PlexConnect. While overall this is the latest instance, about 10month ago (ok, just saying a number here), we added a date to that string. Not sure if I always remember updating it, but the current version shows adds -101215, as in last December.