I grew up in Cincy and coincidentally am there right now with family for Thanksgiving. Ultimately, it's not bad by any means...good arts & culture, sports, food, accessibility & transportation (not too much traffic), reasonable weather. Personally, it's a bit too provincial for my tastes. Not very hip, somewhat removed from cutting edge fashion & music, not very diverse demographically speaking... I left after high school, lived in NYC, Taipei, Dubai and currently LA. I love coming back for a visit tho as it has a "small town" feel even tho' its a moderately large metropolitan area.
I'm using quite a broad brush here, but the city has a very East/West dichotomy... East being more affluent, "cultured", white collar.... West being more workaday, blue collar. (I realize this is a stereotypical generalization that lacks specificity but is generally true so please don't flame!) Anderson Twp. where I grew up is a typical middle/ upper class suburb w/ very good schools, lots of open green space and most of what you'd expect. My family now lives in Hyde Park which is a bit older community w/ historic homes, lots of character, good schools (but many private) and is closer to downtown. Other areas you might check out are Loveland/Indian Hill, Mariemont, and maybe Terrace Park. These are all East side communities in the mid-up range. If you want the wealthy, swanky hipster area, check out Mt. Adams.
Cincy does have great food, a world class art museum and orchestra, two pro sports teams (altho' the Bengals are questionable sometimes!
), very close to Kentucky in case you were wondering, and a huge casino project in the works. Our airport absolutely sucks, is monopolized by Delta and has been rated the most expensive airport on average in the US for something like 5-6 years running. On the other hand we have Graeter's ice cream, which you will soon come to realize is our best kept secret and the world's best ice cream! Really!
If you have some specific questions PM me.... no worries. Hope that helps.