I read it all too and I thought it sounded very positive.. as usual! I agree with Mishka that you two seem to share a common connection that excludes alot of other non-muso folk... and muso in your particular field even.. its like, you are in his world, you understand it and he knows that you do, they are threads that still exist between you. My Mum used to talk to me about that.. send him a link to something about music (for us, its guitar based!) and keep the threads alive..
As for you saying.. "I'm not sure if he sees me because he wants to, or because he feels obligated? Or if he would make the time to see me if it wasn't a limited-time-visiting-from-out-of-town-opportunity sort of thing? "
..my take is there is NO WAY an exBF would continue to see an exGF 2 years after the initial problems started before they split up, becuase they felt OBLIGATED. No way. Take it on face value.. if he sees you, its because he wants to see you. As I often have said thouygh, I cant work out what his motivation is, whether he genuinely just wants to be friends, or some other reason. I sort of wish you would check out his FB page to get more info on his life... put us all out of our misery!!
As for your next move.. didnt he say to let him know when you were playing somewhere? Might he come, or did I get that wrong? xxx