It occurs to me that we have numerous people here that live in outlying areas where there are no ska shows (or too few), so maybe I can give some helpful advice ...
BOOKING SKA SHOWS 101:1) BOOK SOMETHINGThere is no substitute for someone, somewhere that actually does all the chasing down of the details to set up a show and make it work. Every successful scene has people that do this all the time. If you're not willing to do it yourself, then recruit someone else. And if you're willing to do neither, than you have only yourself to blame that nothing is going on ...
2) USE THE SMALLEST, MOST COMFORTABLE VENUE POSSIBLEIt's a proven fact of human nature that when you walk into a really big venue and its mostly empty, you judge the show a failure and often the bands who played as well. Plus, it means very little interaction -- fans to fans or fans to bands. If there is a lot of "hiding room", people tend to use it. And all of this makes the show harder on everyone, including those who really want to dance and the bands who want to interact with a live audience. Put that same audience in someone's basement and you get the exact opposite situation. It becomes a lively party. It's very critical to use the smallest possible venue you can, because it'll save you money (always a critical thing) AND make for a better show, actually. And of course, try to use the most "comfortable" venue you can -- in other words, one that whoever you're trying to draw will be happy to attend. Atheists don't like churches, sXe don't like bars, etc. You'll have a lot of trouble drawing to the show if people don't like the space.
3) ALWAYS USE LOCAL BANDSWhile it always sounds more exciting to start off with bigger, out of town bands, the reality is, they're probably suicidal for you to book in the beginning. They want a lot of money, which you don't have, and they have high expectations, which you can't yet meet. Now, some out of town bands will play for "gas money" (ALWAYS pin down what that means to them!) and are very entertaining, but they probably won't draw enough to pay for the space or the sound system or maybe even the gas money you give them. Local bands, NO MATTER HOW BAD THEY ARE (and even if they're not ska), are
CRITICAL to making a local show work. They do the flyering and more importantly, they bring along their friends and family members to actually get someone in the door that's paying. You supply the show and they supply the fans to make it work. It's really the only sure way of getting off the ground in the beginning.
4) PROMOTE LIKE CRAZY, BUT REALISTICALLYThere is a common misperception that more hype equals more turnout.
IT'S ABSOLUTELY NOT TRUE. Good promotion merely makes you aware of something, but it can't make you care about it. How many ads do you see every day advertising products you don't buy? Think about that. Promote every way you can, but be realistic about your efforts. Handing out thousands of flyers for a little show that only a handful of people care about is a huge waste of time and money. It won't make anyone more likely to go, unless they're already going and need a reminder. Most show flyers are reminders, not motivators. Think about it.
5) KEEP IT SIMPLEIt's amazing how in the beginning, everyone wants to be so ambitious. It's not a bad idea, except when it gets in the way of reality. And it usually does. Booking bands you can't really afford, reserving a venue you can't fill and hyping the event beyond all reasonable expectations is merely a standard recipe for failure. And its very difficult to build on failure. But any success, no matter how small, is the building block for more success. Do the show in someones basement with all local bands and a borrowed PA if you have no idea if anyone will show up. The critical thing is that whoever goes has
FUN. If they have fun, they'll come back. If they don't, it'll be that much harder to get them back next time.
CONSISTENCY counts more than flash. If your shows are consistently fun, one that's less fun won't really hurt you. But if your first show isn't fun, you have a very big problem ...
Okay, there's plenty more, but that's a good start.
Also, do us both a favor. Clip
portions of this to comment about and not the whole long thing, okay?

Lastly, this is from the School of Hard Knocks. I've been doing shows since 1997 and I've learned a few things. I also learned a lot by checking out how early US ska bands like The Untouchables started the LA ska scene from scratch. Hopefully this will be of some use to some of you ...