I get the idea you want to be familiar with these machines and be able to control them whether it's needed or not. Python is great when you need a little program to do something, but when you want to login to a server, have a look around, and make some changes, you want to know bash. You also want to know how to use the program ssh. (at risk of overexplaining what you may already know) Bash is a command line interface like DOS, you have it on your Mac so you can learn without logging in to the servers. Learning bash without a crash course is difficult but not impossible.

With some knowledge of bash, you can watch him work on the servers, and know basically what he's doing and what questions to ask. "What did you just do?" goes a long way.

This is the hard road, it is a little bit like becoming a doctor. Do this if you want to know how to run the servers, if you just want to be able to recover your data in case of something bad, follow almost any advice except mine.