How are you hanging your antenna? Dipoles for 20m and lower are typically set up in an Inverted V configuration, which should work fine with the 10m mast you already have.

As someone who used to troubleshoot an extremely complex system for my day job, I can say I've worked my way across the entire bell curve.

Python or Perl. IIRC, I've seen systems with a Perl install by default, but not Python.

It's definitely great in theory until you inherit a codebase with no tests, poor documentation, and numerous reported bugs already live in production. Even better if it was written by people hired because they could do other things better than they could code - which looking at some of the unlabeled wiring messes we were left, isn't saying a lot.