Cody, I'm about a year into the local art show circuit in the LA area. I think next weekend will be number seven for me, so I'm still a relative newbie. Since all the shows I was interested in doing required a business license, I got that set up and did the DBA thing that's also required here. I'll be doing my first sales tax filing in a few months, so I don't have any experiences to share there...yet. I've kept good sales records, but I learned when I did my taxes this year that I should have kept better expense records. I got a nice deduction due to business losses, but if I'd kept better records I could have shown an even bigger loss, and therefore paid even less income tax.
Like Barry, I'm also using ProPay for my credit card processing. For my estimated 6 to 10 shows a year, it was the most economical option. There are LOTS of companies who will help you set up a credit card account, but ProPay is the only one I found that doesn't have some type of monthly charge. If you're doing a lot of shows, the other, electronic options are more viable.
I also accept personal checks. Before I started, I did a lot of research and asking various questions of vendors at shows. One guy in particular told me that in 16 years of doing shows at least once a month, I think he'd received only one bad check. He figured it was worth the risk. Keep in mind he was selling artwork, not low-cost crafts, so he was dealing with higher-end clientèle.
And that brings up positioning. Bill's points are very valid. You can be Cody the Wood Turner, selling at craft shows, or Cody the Wood Artist, selling at art shows. Both guys can sell stuff, but one will be selling pens and pepper mills and bottle stoppers in volume, and the other will be selling semi-functional bowls and other vessels, a few at a time. In the local circuit here, there are several woodturners. There are a couple guys who specialize in pens. There's another who specializes in little pill boxes and desk accessories, but he has a few small bowls and hollow forms on the back shelves. There's another similar guy, but he stocks mostly bottle stopper sets (with holders and corkscrews) as well as other kitchen stuff. He also has a few nice bowls and hollow forms, but he always seems to have the same ones, so I don't think they are moving off his shelves very fast. All of these guys are turning as their sole income, and the small stuff is what makes then money. They get into production mode and churn out a pile of pens/bottlestoppers/business card holders, etc. They make very nice stuff, but sell in volume at a low price point.
I'm the odd man out in the circuit. I'm referred to as "the bowl and hollow form guy" among the other turners. (We all send potential customers to each others' booths.) That's primarily all I show, aside from a dozen or so pens and maybe five or six bottle stoppers. I'm trying to position myself as an artist as opposed to a crafter. I don't have the booklets Bill suggested, but I can (and often do) tell a story about every piece I have displayed. At the shows, I refer to my "studio" instead of my "shop". I'm intentionally seeking out the more affluent "art shows" instead of the lower-end "craft fairs". Both types of shows can cost the same to enter, but they attract different crowds. My dream client is the one who walks into the booth, sees a hollow form and says to her husband "Wouldn't that look perfect on the table in the Tahoe house?" I'm looking for people who are willing to spend $150 to $300 without flinching. On the other hand, I figure for those sort of prices, I need to make as high of quality work as I can. It's my motivation to try to get better, and it makes me more meticulous about the details (like sanding scratches and finish blemishes). I've still got LOTS of room for improvement. I know I'm a relative beginner and no better than many, many other turners, but by putting myself in an environment where quality and perfection are expected, it helps me improve my skills faster, I think.
I don't sell a lot of volume, but my price point makes up for it (since I position my work as art). If I sell one or two pieces, I can generally pay for the show entry fee, which has ranged from about $250 to $350 per show. So far I've had two shows where I didn't make my entry fee back, but I've had others that more than made up for those losses. But unlike the other guys I mentioned, I'm not relying on my sales to put food on the table. Any sales above and beyond the entry fee are gravy to me. I've got a day job, so I'm not as reliant on the income from turning. In fact, I'm still not even making a profit, by the time I include the cost of turning tools and equipment, materials, and consumables. But the sales so far have helped support my woodturning habit. I tell my wife I'd be spending the money turning anyway, whether I was selling my work or not, so any income from sales is like found money.
I could maybe make more money if I went into production turning and did pens and bottle stoppers instead of bowls and hollow forms, but I wouldn't be having any fun. I'd rather turn what I want to turn, and sell less. With perseverance and time getting my skills and reputation built up, it may ultimately be more profitable in the long run anyway.
Another unexpected bonus from doing the shows has been having fun with LOML. Her help has been vital and appreciated. She really doesn't do much in the booth...lets me do all the talking, but with her there I have company, and someone to cover for me during bathroom breaks. Plus, she enjoys checking out all the other booths, people-watching all day, and the camaraderie among the vendors. The vendor community here in LA has been very helpful and hospitable to us, and that's made things even more enjoyable.
Cody, your work is easily in the "art" category should you decide to position it (and yourself) there. On the other hand, I'm sure you could do well selling craft items if that's what interested you the most. Whether you make any real money or not depends on a lot of variables (including your location), but I'd say go for it.