I have a lot of friends that are excellent musicians.  They work regularly and are well-regarded locally, in Tulsa.  But Tulsa doesn't pay much, so it's definitely a labor of love.

From what I've seen, you either have to travel - still being a "bar band" doing cover songs - or you have to go to a city that has a bustling music scene, like Austin.  And either way, you have to be really lucky.  Luck beats skill any day.