the kentucky side and the cincinatti side form an interestingly coherent cultural enclave. the area is historically populated by german catholic immigrants. in kentucky, they say "northern kentucky" to refer to the three counties next to cincinatti because of this. weird stuff. also a lot of appalachian culture. woke cincinatti actually used to be a place where it was illegal to call someone a hillbilly.

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.

There's a good of southwest Ohio PSL branch! I'm on the opposite side of the state but I coordinate with them on statewide stuff now and then.

The coolest area of Cincinnati is pretty undeniably Over The Rhine, but it's undergoing intense gentrification right now.