Ooof. Booking agents have always frightened me - I've always done it myself. Of course, I've also never gone too far beyond the "local level," (other than occasional shows out of town). Actually, no, that's not true - a side-project band I played in once had a booking agency who was horrible. They kept telling us about potential shows far out of town days before the shows in question, and kept trying to get us to play places that we didn't want to play, threatening that it would be bad for "our career" if we didn't. Ugh.
As for booking yourself, in my experience it's always best to plan a month or two ahead, because local clubs (at least the ones that are any good) are usually booked that far ahead. If you know the individual booking people and you're looking for a quick-turnaround thing you may always get lucky (they may call if a band drops off a bill), but generally, plan ahead.
Also, get organized. Start a spreadsheet or a google doc so you can keep track of everything. Call around to all of the clubs, get their addresses and contact info and find out who's booking them (and get their contact info in case it's different than the clubs). Send out press kits, or e-mail the folks who like to work over e-mail. Be polite but persistent - my college band got our biggest gig at the time because I called the club's agent every two to three days and left polite messages on his machine. Sadly, he then tried to screw us out of our payment after the gig, but hey... it was a great show.
When you're sending stuff, always make sure that whatever you send out looks good, but don't go overboard. I used to book shows, and would get mailings from local bands with folders emblazoned with their logos and stuffed with testimonials... sad to say, I'd usually pass those up (and when I did listen, it was almost always the case that they were overcompensating for the music with promo materials). But the cdr with the band name in sharpie would get the same treatment. Bands that clearly took pride in their work & the packaging, and didn't send too much material with the CDs (generally a one-page bio/press release is plenty... maybe an 8x10 photo if you want, but those so often look ridiculous) would usually make it to the top of the pile.
Persistance and organization are the main thing, though - keep track of who you called, so you know when to call 'em again.
As for ca$h, it's always been my experience that when playing at clubs, a portion of the door, divided between the bands, is the standard. Some clubs do it differently (one NYC club asked each customer who they were there to see, so we only got paid for the ten friends who came out to see us... and we'd comped five of them).
Sorry for the ranting - I hope it's helpful. This has just been my personal experience - there's other sources out there too. You can check Book Your Own Fuckin' Life -
http://www.byofl.org/ - and stuff from the old Simple Machines record label -
http://www.simplemachines.net/mech.html (that was a mid-90's indie label - some of the stuff may not apply so much anymore).
Oh, and if you're at a college, cuddle up with the Student Affairs / Student Life / Entertainment people - they've got a budget that they've got to spend every semester on entertainment, so they may as well spend it on you! College gigs were always the one sort of gig where one could dependably make money and have at least semi-decent sound.
), but if you can avoid that, it's always good...
