Brenda, if the rest of your oil portraits are as good as that one you can charge a lot more than $500. Maybe start at $1,000 and see how it goes.
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The other consideration is repeat customers. If I do a commission for someone at $500 and 6 months later they want another portrait of their other child, they might not appreciate paying $800 for "the same thing". If I start at $500, I have to be willing to increase my prices gradually. I would be wary of giving repeat customers "deals" as they might come to expect it every time and want another $500 portrait when my work now costs $1500.
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My repeat customers pay whatever my going rate is at the time, regardless of what they've paid in the past. For example, I'm doing a second portrait for a family whose older child I painted two years ago. At that time they paid $4,900 for a three quarter length portrait with a very complex background. Yesterday they signed a contract for $7,800 for the same type of portrait. My prices are now more in line with what people charge nationally for this sort of work, and I've had some higher profile commissions in the intervening two years, which is why my prices are higher. I'm told by folks who really know the portrait business that my prices are still on the low side, however.
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