Let me back up a little, I would not suggest you try to get into a gallery. Marketing through a gallery is very different from the kind of commission work we do as portrait artists, and has it's own set of rules.
When I said hit the galleries I meant to see the tone of the paintings being commissioned in a given area. The galleries in Santa Fe, New Mexico have a different flavor than those in New York or Atlanta. I sell better in the mid to northern parts of the country than in the deep south because my paintings tend to be deeper, richer, and more tonal the "Southern" portrait that was in style when I first started out. An area rich in Victorian Art Galleries, or galleries with paintings drenched in the orange/red light of New Mexico will give you an idea of what kind of portrait the population might want to place in their homes.
One final thought, I doesn't matter how an area is for portrait sells. You are only selling one painting, initially. Dallas is a good place to start if you have support there. Atlanta might be spectacular in general, but if you can't get work there, it's bad for you. Minot, North Dakota may not be the hot spot of the portrait world, but if you are painting the president of the bank, hey, it worked for you. The location of the commission is not important, what is important is how you sell yourself and how great a job you do on the portrait. Everything grows from that.
I said in a different spot on this site that one of the keys to success in this business is a lot of eggs in a lot of baskets. So the more territories you are working, the greater your exposure. Just don't overdue it. Become as much a portrait fixture in each of your territories as you are in your own local area.
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When you say the first few times for you "it didn't take", did you go back again a few years in a row with the same patron, or was it just that you hit the right region eventually?
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I hit the right region eventually. I am tenacious, but I know when to stop beating a dead horse. Something I tell my students, and a piece of advise which is counter to that offered by one of the more visible art marketers, is that you can't talk anyone into buying a portrait. They either want it or they don't. This is not like selling sports equipment or aluminum siding. A client cannot be "hard sold" into buying a portrait. So I do my best shining. And if they aren't interested, I shake their hand, say a polite thank you, and steal into the night.
Peggy