I actually just had this chat with a friend the other day. From the way he made it sound, it's actually easier (and probably more affordable) than I thought. There's a really good event park close to my home in Broken Arrow, Oklahoma, that'd be perfect for a bicycle swap meet. Even though it's an "event park," I just call it "the big parking lot" because there are more parking spaces than there is actual "park." I bet if I got in touch with whoever's in charge of that park, I could probably have something set up on a weekend. The biggest concerns I have are the potential costs of reserving that space for the swap meet, running the swap meet (something I've never done before,) advertising the swap meet so more people would know about it, and how many people would travel to Oklahoma for a new bicycle swap meet.
I wouldn't be too surprised if the fee for running a swap meet at this park would be $0, but I also wouldn't be surprised if it costs at least a few hundred dollars instead. That's my first biggest concern, due to my... limited funds right now, as well as charging fees for vendors to pay it back.
My next big concern is actually running the swap meet. I know a lot of folks just want to buy/sell/trade bikes and bike parts, so I may start there, but I also know that a lot of folks love to show their bikes and even race them, based on my experience at Buddy's Pedal Fest last year. I'd probably just start off small, with just the swap meet, then if all goes well from there, I could build on it.
My third concern, though not as worrisome as the others, is getting the word out about this swap meet. I know I could post it here on The Cabe and Rat Rod Bikes.com, and I can advertise it locally on Craigslist, but I'm sure that there's at least a few groups on Facebook that'd be interested too. Problem is, I don't have a Facebook account, nor do I really want one for anything other than Marketplace. Maybe I could ask my parents and friends for help on that, but I don't know. I'm sure if I advertise it on the bike forums and pass out flyers at my local bike shops at least, I could possibly see a decent turnout.
And lastly, my biggest concern: I don't know how many people would actually show up to a bicycle swap meet near Tulsa, Oklahoma. There doesn't seem to be a lot of vintage bicycle activity around here, and based on the activity I've seen on FBM and on the forums, I'm about 3-4 hours away from most vintage bicycle hot spots. It probably doesn't help much that the location I have in mind isn't in some scenic downtown district where folks could look around and grab a bite to eat while they're at the swap meet either. So, I don't know how well this event would do the first time around.
I definitely want to explore the possibility of starting my own swap meet, but I'm sure it's a lot harder than it looks.