I very much like The Jolly Wagoner, and The Thirty Foot Trailer. They aren't about musicians, but if you hope others will relate to your experience, a generous way to start is to try relating it to other people's experiences somehow. If you're picking ragtime tunes to pay the bills, maybe you can relate to someone who's picking rags to pay the bills. So what if that's a blues song instead. All that said, I also like the Cowboy Junkies' 200 More Miles, which is straight up about travelling musicians.

I was leading a writing workshop once that someone decided to derail into a Write What You Know symposium, merely because I was doing an observational exercise without any first-person commentary. Writing what you know makes sense as long as it isn't taken as an invitation to be a self-absorbed windbag. I think we write to discover what we know, which puts the reader and writer into a shared experience (or at least the illusion of it) rather than a tidy presentation.

For better examples of books and stories, a lot of Nabokov's stuff is from the point of view of a writer--one he has invented for the purpose of making his boring personal concerns more striking and strange. Not everyone can cast their concerns in such disturbing tales as he does, or would want to, but I find it great fun. Borges went so far as to write fictional reviews of books nobody had actually written. What did Shakespeare know about being a maddened King with three daughters? He knew about the problem of proportion in representing things, so he wrote about that. I really believe it comes through somehow if the writing is a process of discovery for the writer, whether or not the names, situations, and props change much.

   Sorry--I'm still a little miffed about having my little workshop ambushed!