It’s been a moment since I lived there, but I’d say the KY side would be less desirable based on your stated needs.

I lived in the Clifton/ northside area near the university, that’s a pretty good progressive area. Oakley would probably be pretty good too, a bit more residential / young families etc. I was in grad school and the cooler younger profs I had tended to live on Oakley for example.

OTR might be interesting as well, not sure how things have gone since I was last there.

Mass transit and diversity are… touch and go in Cincinnati, but it’s generally a decent place, I enjoyed my time there. I’m from Baltimore and I’d say cincy is about as historically racially segregated Baltimore is, which is to say: a lot.

I’d say it’s definitely possible to do mass transit and bikes for sure, but there are thing a where a car makes things much easier.

Also I’m not trying to shit on Covington/newport, but it’s just probably a slightly less good fit based on all the standard reasons you’d imagine. Newport in particular was a kind of party night destination when I was there. Maybe it’s massively changed though.

Take what I say with a grain of salt—it’s been a decade since I lived there. Easily my favorite “big” city in Ohio though. Great bars and food, good topo, some great parks. A personal fav of mine was walking around spring grove, 19th cent huge cemetery. That sounds morbid, but it’s also an arboretum and very beautiful.