I actually do want to learn something new (I guess I am doing some thinking out loud with this post). I know what you mean about your head swimming. For me (and I am not saying this applies to anyone but me) C++ always seemed like an insurmountably huge language. I know that may sound silly to some, but I never have seemed to be able to get into it. I will grant that part of the problem was lack of motivation (I did not have a real need to code something in C++), and part of the problem was a lack of something "real" to code on to practice my newly learned concepts. Example exercises can only take you so far.
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I like your advice - it seems to me that doing this project in C & Python would be fun, and a fine way to get an idea of the level of difficulty to produce a functional program (with identical functionality) in each language, with the benefit of doing some hands on learning of Python.