To be blunt, I think you are overshooting.
Pitt is great and you’ll get in. American, too, if you demonstrate interest. But like Vassar they are not
Also, counting grad students, U Chicago is large. Undergrad is nearly 8k and grad 10k it doesn’t fit at all your want small like Vassar. So do you prefer a mid/large like Pitt/Chicago or small like Vassar ?
Bard was an interesting suggestion. Bates too but will be hard RD.
Bucknell and Juniata are both Shepherd Schools - which have programs focused on poverty. Bucknell is a likely/target and Juniata safe. Macalester would be a worthy target as would Brandeis, which is rated a top school for kids caring about the community.
For law school, where you go won’t matter. It will matter in the sense of you having a great experience. But the top law schools - including Penn, Harvard, and UVA - have more than 100 colleges represented in their first year not large class. Penn more than 200 through the 3 years.
Good luck.