These are nice Mike.
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I think that would have it's own particular set of challenges knowing that the subject was capable of critique.
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You are absolutely right, that's probably why most artist stick to painting friends and relatives over fellow artists, unless of course they have years of experience behind them. It is interesting to see though, that the generations before us, did not shy away from this intimidating task for some of the various reasons I have listed before.
Well, I decided to take the plunge and have asked a fellow artist friend, who has received her art education at Julliard and is a portrait artist herself, to pose for me. Due to her schooling, I am sure I will hear critique, but that is welcomed and it will create a collaborative work environment. I have always wanted to paint her, because she has such a chiseled, classical look about her and I just love her speckled green eyes. It will be interesting to see what setting she wants me to portray her in, as the artist or the socialite. Since she loves to chat non stop, concentrating on capturing her while chatting will be the biggest challenge and learning curve to overcome.