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HI Judson -
When I was in college, I worked at Busch Gardens for two summers doing just this sort of thing. It was great practice and a good confidence builder. We did profiles in pastel with a very limited palette and a pretty canned approach. It took 15-20 minutes to do. Possibly other theme parks would be willing to allow an artist to do this as well, for a fee.
In the mountains near my home, there was a gallery advertising for a street artist, I guess to add "atmosphere" for the summer visitors to the area. Someone drawing from life is quite a draw for a business, because folks gather to see what the artist is doing.
Fairs are a way to go too. For example, three years ago, I got in practice by doing profiles in my school where I work at $10 a pop (took 10-15 minutes, charcoal). I started out by doing them at our school's fall festival.
Good luck with your endeavors!
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