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The one thing you can guarantee about the system python is that it's exactly as up to date as the system itself needs it to be. That's why it's there: it's not necessarily for you, unless you happen to be writing something system-level.

Anecdotally I've run into more problems with python than with ruby over this issue, but I think that's just because I'm more familiar with the parts of the ruby ecosystem which let me draw a clear dividing line between system-ruby and my-ruby. My impression (which is probably out of date) is that python tooling tries to bridge the gap, and in my experience that's not worked well, to the extent that I just don't try to use python for anything on OS X.

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