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I have 4 daughters and a stepdaughter, ranging from 1 to 13. I understand what you're going through! The way I'm working on their composition, and maybe you can use this, is to know that their outfits are a huge part of the composition. A big white swath across the middle of the canvas isn't the most interesting thing I could think of.
Happily, we have about 40-50 dresses among them, since we save EVERYTHING. It's not too difficult to make an interesting and varied composition using different dresses with different styles, patterns, etc. They coordinate, but aren't all the same. I chose summery florals, from large to small prints. While I'm painting it, I may alter the pattern or color slightly.
Maybe you can ask the mother to see the girls' closets? More similarities will look more formal, more pattern will look more casual. When she says "timeless" I hear "not much like they look day to day" but the nice things they wear for holidays might be rarefied enough.
The issue with the 12-year-old is probably just one snippet of an ongoing series of arguments between them. The mother might, though, be grateful for the opportunity to say "well, the ARTIST says you need to wear this one, it's not up to me." It will be difficult to please everyone, but you might skate by on being the professional opinion.
Mike, Jeff, I hear ya.
Good luck!
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