Booking
It's important to designate a single person in the band to handle bookings, even if you use an agency. You don't want any embarrassing date collisions when multiple people get gigs on the same date. Nor do you want any confusion about who to talk to. It's key to have one person coordinating this aspect of playing live. Give them a booking cut of each take, so that they are getting something for their time and efforts.
Once you designate someone, make a band calendar and mark all of the dates that the entire band can be available for gigs. Mark all dead weekends and evenings clearly for the booker. Sometimes, this is best done using a Yahoo account, or other free calendar sharing programs, so that everyone can update the same place easily and so the booker can check it as it updates.
The person doing booking should be a "people person." It's all about the relationships. It's about having a beer with the people who book bands at the bars and also about having a thick skin to deal with rejection. They should also be persistent. And they should have a cell phone.
We hate to say this, but if you can, get a woman to do it, especially if they're attractive. We had a female booker at one point, and it helped our band get gigs, and made for good relationships with the bars. They enjoyed calling us. Most of the venue bookers were guys. Most of the other bands used guys as bookers. We had the advantage. Hey. It's the music business. Do what works! (We realize an exception would be male gay bars, and gay bookers. Again, if that's your scene, do what works! Match the genders the right way and let nature help you book your band.)
You will need a booking kit with a short one-page description of the group and a CD with a sample of your music. It's best to describe your music by comparing yourself to bands that people know. If you're a cover band, that's easy. But you might have a harder time as an original band. Most bands that play original music hate doing that, but it's the quickest way to describe the band in a sentence. Imagine that your booker is in a noisy bar, talking to the venue's agent about a gig. He asks what you sound like, and suddenly, you need to be able to yell it over the bar noise and accurately describe yourselves. You can't say: "Like bittersweet chocolate, with flavors of a sunset afternoon" and expect them to understand. But imagine if you said: "We sound like Elvis was covering Led Zeppelin with a reggae backing band" (that band exists, and it's called Dread Zeppelin.) They'd think that you were nuts, but at least they'd have an idea what you're about in one sentence.
After dropping off your kit, your booker will have to be persistent and keep calling until you get that gig. You may have to play an initial open-mic night to get in and some of these require you to pay for the sound guy. Those are worth doing to start the relationship but not after the first time. We paid the first time we played, but the next show, we got the door. And once we established a following, and had the ad clippings to back up the fact that we were established, we were in much better shape.
Keep in mind that the first time you play at any particular venue, you need to bring lots of people. The bar is there to sell beer, not music. If you need to get people out, throw a party starting after your show. Basically, you invite your buddies out to see the band and then for a keg at your place right afterwards. We did that when we first played live. We filled the place when we played and we emptied it when left. They not only had us back, they had us headlining.
We don't know about booking other cities, but in Chicago, proving yourself at one venue means absolutely nothing to the others. Hog Head McDunna's might love your draw, but when you try to play GooseIsland, you have to play an open-mic night to show that your band is worthy of a weekend. We even had to do that after we crossed the 5 year mark of clippings and experience. It's frustrating but it's the reality. They won't even call the other bookers to prove that you are what you say. They are all in competition. You might have to smile and deal with it, and build your relationships slowly, and separately.
Finally, once you book a gig, do not ever cancel if you can possibly help it. Venues will often ban you if you cancel. Especially on short notice. Beatnik Turtle once had our drummer cancel on us a few weeks before a gig, and we ended up playing the show without the drummer! We called it the Beatnik Turtle "acoustic night." Although it was a difficult gig, the bar was very grateful, and we kept the relationship. We've played there many times since, and that bar still loves us.