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I have heard of artists notifying their past clients and anyone else they think might be interested a couple of months in advance of a price increase. Email is less expensive than a postcard of course, but less personal. I had not notified people in advance of my last price increase, but will next time.
I charge by body part. The complexity seems to be what takes the time, not the number of canvas inches I have to cover.
I offer discounts for multiple portraits that are completed at the same time, or, in one case, for two portraits completed a year apart but where the client paid the full 30% deposit for both up front.
I will be painting five children in a family over the course of eight years, as each child reaches a certain age. They will be paying whatever price is in effect at that time. For this particular family however, price is no object. For another family I might negotiate something else, if they wanted, but I would not hold my prices at a level from several years ago.
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