I am from a suburb west of Cleveland. To start, a few months ago the presigeous London-based Economic Intelligence Unit ranked Greater Cleveland as having the highest quality of life in the U.S. A number of factors were considered and calculated in their system, cost of living, weather temperance and lack of natural disaters, security from terrorist threats, access to cultural institutions, average commute time, health care, education, and recreational opportunities. I am not suprised that Cleveland achieved this ranking, but most people were very suprised.
There are many strong points to the Cleveland area, but the key is you have to know them. There are very few people I have encountered who really know the region. If you live within the Cleveland metropolitan area (Cuyahoga County), you have a large variety of housing to choose from, a variety of good restaurants, bars, and shops, lots of recreational opportunities, good school districts, and simply "things to do" to choose from.
For some reason when people complain about the city about lacking something, it really kills me, because if you live within Cuyahoga County you can find what you are looking for if you are willing to drive no more than 40 minutes.
I think the Cleveland area is a phenomenal microcosm of the the US. What is bad (I'm not going into detail for sake of time), but also very good. It is halfway between New York and Chicago, and I think the result is that it has a lot of assets and appearances of major East Coast cities, but acts a little more wholesome and friendly like the Midwest. I would encourage you to visit some of the highlights of the city like downtown and its Warehouse District, Tower City, and Playhouse Square, and neighborhoods to the west like Ohio City, Edgewater, Tremont, Detroit-Shoreway, and Westpark. Univeristy Circle and all of its excellent museums/institutions, and neighborhoods to the east like Little Italy, Coventry, Cedar-Fairmont, and Shaker Square. Beyond the city you will find so many suburbs. Lakewood, Rocky River, and Westlake are good ones to visit on the West Side. Cleveland Heights, Shaker Hieghts, Beachwood, Pepper Pike, Chagrin Falls, Gates Mills are nice ones on the East Side. More working class communities on the South Side like Brooklyn, Parma, and Brookpark.
I'd say that only when you visit all these neighborhoods can you really understand what Cleveland really is; a wonderful and diverse place to live, perfect for almost anyone.
I will say one thing though. I don't know a whole lot about the South, but I go to school near Cincinnati and have been down to Cicinnati occasionally and I have been into Kentucky. There is something I haven't quite figured out for myself, but I think Cleveland is a very "Northern" city and there is maybe a Northern v. Southern culture I cann't quite explain.