[Chris Saper]

Kim,

I think this is a big red flag, and you are unlikely to get her to like the way she looks at this time in her life. I don't know that you ( or anyone) can get control of the situation.

I say this because I haver made this same mistake - twice, and I should have known better after the first time. My client was very similar to yours in terms of age, appearance, etc, and began by saying she had never liked any photos of herself. I painted what I thought was a really lovely piece, and after she had it for a week or so, she decided she didn't like the 'mood' " I look a bit sad..." I actually painted a second piece , which she didn't like as well as the first. I rephotgraphed her twice, but couldn't come up with anything else she was happy with. After many, many hours of wasted time, I ended up returning her (already spent on my part!) fees.

Some years later she called to say she had purchased a Gift Certificate at a silent auction, and wanted me to paint her! I declined this time, and a mutual acquaintance bought her Gift Certificate, so all turned out OK, although it could have been much worse.

I have declined a few other commissions in the intervening years because I just knew I would not be able to meet the potential client expectations. Even when I could have really used the money.

I worry that if you proceed with this job, you will have 6 people to try to please, and are unlikely to have a happy outcome.