I think this is my least favorite PBF, but that might be because I’ve always hated Family Circus.

Interesting, I'm currently reading a book where something like this is a major plot element:

absent father encourages preteen daughter to dress "as a woman" by leaving way too much money under her pillow, knowing that his wife is strictly against it.

Preteen believes her mother is restricting her freedom against her father's will, ignores her warnings ... disaster looms.

It's a fantasy novel in a more-or-less 18th century society with magic, so the disaster is very palpable yet at the same time not what it would be in the real world.

I see Junior will grow up to be an investor