Thanks for your suggestions, Mike and Mari.
I was actually hoping for some ideas about how to orient the picture, and which hand treatment and how much of the model to use, but you've all certainly re-sensitized me to the importance of just saying "No" when the subject's wearing something so problematic.
My specialty is "portraits in a natural setting," so that's what people expect when they commission a painting from me. I try to find a background that says something about the individual and that enhances his or her persona. Sure, I could go in and try to catch her in her office but I have no idea what I'd do with those photos; it's just not my style.
With that time line facing me I've been working on it today and I've got the thing blocked in now, using the first pose but cutting her off just at the hem of her shirt to avoid those rails, which bothered me, too, and then using the head I posted. I ended up with a horizontal orientation because it worked better for getting both hands in without making her too small. I'm going to soften those harsh shadows in her face and also dull the red, leaving only the highlights of the shirt bright and bringing in red in her ears and lips and so forth. And I'll show you what it ends up looking like and you can all say, "I told you so!"
But nonetheless I think she'll like it because it's what she wanted.
Oh, the portrait's going to be presented at the annual NJ Conference of Mayors gala and it will hang in her living room in Stone Harbor, right by the beach.