Just an update on this, as I went in to see the doctor today.

He believes I have ulnar neuropathy. When I came home and looked that up on Google. The symptoms described seem exactly what I've been having. He made a few suggestions of what to do, including making sure I sleep with that elbow straight and not bent, and some changes to how my arm rests when I type to alleviate pressure there.

Hopefully a few preventative measures will improve it. I'd rather not have to have surgery or anything.