Great piece, Todd. Great advice. What you're saying about the music itself reminds me of when I used to play in a wedding band. Very, very similar situation.
FWIW, I toured for about ten days in the early '90s as fill-in drummer in the backing band of a very big deal (at the time) singer. He was a neighbor. I did it for no pay, per se, but when it was over I was the happy owner of a new big screen projection TV and a top of the line VCR. In a store, the stuff would've cost about five grand.
Of course, I never got to use the home theater equipment because I lost it to my then-wife soon after in the divorce my week of thrills and anxiety was one - but only one - of the many causes of.
Oh yeah, after the divorce I was no longer the singer's neighbor. I lost the house as well.