Where would you rank python in terms of difficulty in learning enough to do useful stuff?
one of the easiest,
Python is awesome I love it.
Its just really cool because there is a thousand and one ways to do anything. You can make programs look so very weird and dense that no one can even understand what it does by reading it except you - or you can make them very straightforward and look almost like prose
I haven’t learned very much of it yet, but I’m very glad that blender is the peanut butter to python’s jelly if you know what I’m getting at 
Its very easy inded… and the sintax is really elegant. Once you realise the clearness and power of indentation and line breaks to format the code, you will end up hating all those ; and { } in most other languages.
I your experienced in more than one other language, I think you’ll find it a doddle. I wrote most of Midi_Import_X (see my sig for links) as my first piece of code in python and found the language itself pretty straight forward. Obviously, I feel like I may have missed a few tricks on the way and that the code I have written is far from optimised, but… It does do the job and is complete with a GUI and hooks into the blender api.
Don’t be scared, wade in… it isn’t too tricky.
It’s pie to start with if you have even a tiny bit of programming knowledge/aptitude. The really nice thing though is that once you are started you can go as deep as you want. High level algorithms and abstractions down to low level hardware wrapping in C - python can facilitate anything you want a computer to do. Go through the introductory tut (first entry in the help file), it will lead you through all the basics.