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Here's my two cents worth:
Step 1. Create half a dozen portrait samples in oils and other media, just under life size, of the high quality seen in some of your best work: your painting of the girl pinning up her hair, the portrait of the red haired man with the glasses and the head and shoulders portrait of the girl with dark hair and the red dress. (You might want to try a variety of subject matter for your new samples: one painting of an older man in a suit, a woman, a girl, and one painting of a little girl and boy together, for example.)
2. Delete many of the lower quality portraits now on your site.
3. Once you have six or so great new samples, start charging $1,000. for a head and shoulders in oil. (I can't comment on pastel or charcoal prices since I don't do that kind of work.)
4. Promote your work among people who can afford it. Donate to some high end charity auctions to get your name and work out there.
Good luck!
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