My wife and I talk about moving to CLE once in a while. (We come pretty often to visit relatives.)
From a visitors POV I'd like to point out some pros and cons that I've noticed.
First, Dan, you keep talking about the high crime rate in NY and the peacefulness in CLE, but when we've ventured just a few blocks from the Jewish neighborhoods we found ourselves in very unpleasant areas. Judging by the 'residents' I would not want to find myself there anytime - armed. However driving in the opposite direction lands you in some of the most beautiful shopping areas I've ever seen - and that includes areas like Miami, New York and L.A. The malls are stunning which is a surprise because most of the neighborhoods I've seen have small old homes. I guess they save their money for buying clothes.
The times I've been there (spring, summer, fall) the weather was beautiful but it's the winter that scares me.
I think what's really keeping me away is the idea of being so far away from all the activity that makes up the vibrant, buzzing, northeast communities. Just things like going out for dinner at a nice restaurant in Manhattan or visiting relatives nearby. It would be so strange to be so far away.
Another nice aspect is the cleanliness. There is barely a paper bag to found in the street. Hard to imagine, but really makes the city. I also love the 'oldness'. So many houses have these enormous oak trees on the front lawn and people seem to really care about their landscaping but not in a pretentious way. Older houses also have a kind of charm; they all seem unique in some way unlike the cookie cutter developments seen all over Monsey/Lakewood etc.
I'll try to think of more things. We are really looking for an easygoing place to raise children without the rat race mentality or the crushing hyperstress that so many people seem to be living under.