This would be nice. I'll do this at some point.
Yes, if you put an image in a folder that's in the application directory as long as you name it the same name as your team you'll see it in the editor. I've put all the APF and NFL logos to start us off.
There is definitely a section for each team which points to the playbooks. Just need to find those offset locations. It makes sense what you said about the playbook name changes.