It might be interesting to talk to Mark Sink at gallerysink.com in Denver. He's been my dealer for years. I don't know if he'd say he's been successful from a financial standpoint ... he's downsized from a brick and mortar commercal gallery to a non-profit art-space to a private dealership / curatorship run from his home, mostly because of economic pressures. But I don't get the impression he has regrets. He's well connected in the art world, unlike a lot of people who try this (on the board of the new contemporary art museum in Denver, and a former Warhol factory member) so I think his expectations have been realistic. He may have some ideas.
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