I'm all for coffee too and go for it as my default. It does limit options though because I feel like you're not going for a caffeinated beverage in the evening, so that rules out meeting after work on a weekday. Immediately, you're down to two days then. But this might just be an issue for me because I date too much lol
I have had several women seem completely flummoxed by my insistence that we go 50-50 after the first few dates. It's honestly as if they never encountered such a thing before. I don't know if maybe that's reflective of Miami culture or what.
But yea, in general, I have a massive amount of respect for anyone who insists on being equal from the jump. I'm also okay with anyone who wants to start going 50-50 after a date or two, and I outright refuse to always go 50-50.
I get where your son is coming from. It feels like you're paying for that person to be there! I know personally that the threshold for where i would go for free versus where I would go if I have to pay for it is much lower. I don't want someone coming out with me just because the whole outing is sponsored.
It's a complicated dynamic!