My daughter recently chose between UCLA and Kenyon and i posed a similar question. It started a great thread in which many helpful people talked about the big vs small of those two places. They have some obvious parallels to Cal and Oberlin so maybe it will help you.
My daughter chose UCLA. I was taken by Kenyon and she really liked it on her visit, but on Bruin Day at UCLA, she LOVED UCLA. She knows she’s going to learn to hustle and is looking forward to the challenge.
As a Bay Area resident, we have been to Cal a few times and it was our first official college tour when my daughter was a sophomore. She loved it. Great campus, fun surrounding area. People’s Park and a few blocks of Telegraph definitely have a homeless population. But there’s so much happening that it isn’t a defining characteristic of the Cal experience at all. Housing in the area is pretty insane. Friends kids have paid ridiculous amounts of money for crappy shared rooms, but also, no one seems to mind. A good friend’s daughter loved her time at Cal, graduated last year. She was in the triathlete club, a cognitive science club. Cal does have NIMBY problems, as made national headlines a few months ago but it’s worth seeking out other parents to see what’s really happening.
My daughter’s boyfriend’s sister graduated from Oberlin last year and she also had a great experience. Her advice to my daughter with choosing a liberal arts college was to really try to get to know who your classmates are, because they are going to be all you have for a social life and friendships in an isolated location. Follow the Class of 2026 pages, read the bios, look at the pics, DM them. Are they people you can imagine being around for the next 4 years?
Good luck! Great choices to have!