OK well I've been playing guitar for about six years new and in the last three years I've been taking a lot of paying stuff. I think the formula for success is limiting yourself to one or two people in a band and playing acoustic sets. I've played in cover bands that get paid about 300 bucks for a show but where I'm from (Portland) there's literally hundreds of places to play and thousands of bands so most bars and clubs don't need to actually pay. Some places will though.

So how do I get paid? Benefits, weddings, private parties for rich people, birthday parties and studio sessions. I would stay away from the "band" image and build up a resume with an EP, and lots of experience. Create a business card and hand those out like crazy when your at a gig, say that you usually play for private events and parties and chat everyone up.

It's all about connections, one of the free shows I did where i went to school had some interior design guy who liked my playing and I gave him my card and he lined me up with four private shows for his fashion events and they all payed VERY well.

So plan of action,

Play everywhere and anywhere
have sample CD's and business cards that say (musical performance, for private parties, events benefits etc)
don't try to be in a full band and get paid, play by yourself or with one other person
network yourself, go to shows and network there with other bands too, maybe ask if you can open for them
definitely start a facebook/myspace thing if you want to ever get signed but it didnt seem you cared about that
An obvious one but, be friendly, personable and smile once in a while on stage haha

Brandon