I've been to Cleveland only once, but I definitely like Cincinnati more. From an outsider's perspective, Cleveland seemed kind of rundown with not nearly as much to offer as Cincinnati. I'll probably be going to Cleveland in about a month, too, so my impressions might change slightly. Of course, this video never exactly changes my opinion, hah: http://www.youtube.com/watch?v=ysmLA5Tq ... re=related
Yeah, I've heard that Cincy is a cool city while Cleveland is going through hard times and just isn't that great. That seems to be the consensus.
It's hard for a West Coaster to get a feel for these cities without visiting, but I do value the opinions of fellow Westsiders.
The only city I've spent much time in outside of the West is Philly, which was pretty sweet actually. The old part of downtown was rockin, bro. Certain parts of Philly sucked and were a bit rough, but for the most part it was a cool place. The towns outside of Philly were cool little towns.