Wow.....booking....what a nessesary evil!
Seems like we could do somthing here to help, but I need to put my thinking cap on a bit longer. Technology and the web should be able to automate this process and make it easier?
Nah, I think this is one instance where nothing takes the place of face time. It's called legwork for a reason and if it were easy, everyone'd do it.
I hate slogging through the process of booking, but nothing can take the place of actually walking into a club and checking it out firsthand. And talking to the booking manager in person lets you both size each other up and gives you a much clearer picture of the situation than any online alternative could. At least the first time. After you're a known quantity, the Web and phone calls should be easy for musicians and booking managers.