[rpedela]

"my CS program was woefully inadequate--the standard Java/C++ stuff"

That is the foundation for everything else. You will write much better Python if you are competent with C/C++. The truth is that the major languages are very similar. Yes one manages memory, one does not. One supports the ++ operator, one does not. And so on, but at a fundamental level they are essentially the same. The reason why C/C++ and Java are taught is because these languages are good for teaching the fundamentals: how memory works, data structures, functional vs object-oriented, etc.

Like others have recommended, an internship is a great way to get real-world experience. This is exactly what I did, and it helped me immensely. In particular, I worked for Delphi-Delco Electronics who make electronic automotive parts. My job was to automate testing of the automobile's main computer. Due to safety and regulations, testing was very rigorous so I had to learn how to be rigorous. That skill has helped me immensely throughout my career.

BUT that internship was no replacement for my degree. Without the degree I would be good at testing, but it would be quite hard for me to build an efficient web server because I wouldn't really understand how the CPU, RAM, etc work. While it is possible to learn all the fundamentals on your own, it requires immense discipline which most of us (myself included) do not possess.

That is my two cents. I wish you the best whatever you decide!