My sense is that your prices are much too low. I don't do pastels so I don't know that market but I know you could (and should) get much more than $250 for the work you've been posting.
The key to getting the prices that your portraits are truly worth is to get them in front of people who can afford it. This may mean marketing to a whole new audience.
One reason I don't do pastels is that people usually expect them to be priced a lot lower than oils, even though the time and cost of materials involved are not that much different. "Works on paper" have always been valued substantially less than oil paintings, whether at a craft show or at a Sotheby's auction. It's the same reason I don't work in watercolors any more either.
I love what I do and I'd paint in any medium that was available if it was just for love, but I'm also running a business that is important to my family, so now I work in oils. I like oils so much that I have no interest in ever working in pastels or watercolor again.
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