Answer: show your work as much as you can, whenever you can, however you can.
This is not, by the way, what I used to believe. On my road to becoming a professional artist, I’ve always had my sights set on high-end galleries, with big spaces, white walls and high ceilings. Selling at a ‘crafts fair’ or art market seems cheap to me; yet here are a few reason to do so.
1) You can buy your way in. This is not true for any good gallery; you shouldn’t have to pay to exhibit in a gallery, nor should you have to pay for printing fliers, set up, opening night food, etc (although you might pay a little, especially in a newly-established place). Art fairs are great because ANYBODY can get in, and everybody knows it. This does not necessarily make you ‘cheap’ – in fact by having absolutely stunning work, professional prints and materials set up, you can make a great impression just by being ‘a cut above’ your neighbors.
2) Some art fairs have great reputations – but make sure you do your research. A local crafts fair may not be what you’re looking for. But the Art Fair San Francisco or Gesai Taiwan art fairs (the two I’m looking at for this year) are pretty reputable events that will attract not only lots of midrange buyers, but also some heavy hitters like curators and gallery reps.
Think of an Art Fair like a good advertisement: you’re paying for number of impressions. You may pay about $500 for a 1-day booth at a good art fair. Yes that’s a lot of money – but if you sell a couple paintings and lots of prints, you’ll make it back. Even better, you’ll get TONS of exposure.
Only YOU can make yourself look cheap – avoid that by being scrupulously well prepared and set up. All your work, printed materials, and everything should be super sharp, crisp, clean and professional. You are only as good as your own presentation. Make sure your paintings like amazing, however you display them.
As for galleries – yes, of course you should; unfortunately galleries often approach you – or else exhibitions work out via mutual acquaintances. Once you’re ‘plugged in’, attending the events in the area you wish to exhibit, meeting the right people, networking and making contacts, exhibitions should just sort of happen.