Re: Question for the gigging drummer.
Booking gigs is the worst part of music for me. I do most of the booking for my band, which is a four man (usually) rock and blues band. Dealing with club managers or people having private parties, trying to schedule three months ahead of time, and dealing with bandmates cancelling at the last minute and trying to get subs.... It's only when you get to the gig and are actually playing that it all seems worth it.
HOW to do it? Make connections, be friendly, be persistent, have the whole band act professionally, understand the local market, be persistent, build a following, help the clubs make money, be persistent. Or, you could just hire a manager.