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Can I put in a plug for Cleveland, Ohio? It is only 1 hour by plane to NY, has a great community and several (3 Orthodox) schools to choose from. My son is friendly with the son of a local Chabad Rabbi – they live literally around the corner from us and the shul is one block away to the other side of us. Housing is very affordable. When we sold our house about 2 1/2 years ago, we were asking $150,000 and we were told that a similar house in NY would cost around $850,000! There are 4 dairy restaurants (all Cholov Yisroel – one is a drive up pizza place) and 4 meat restaurants, including a kosher Subway. We also have 3 kosher butchers and 2 bookstores. I know that this may seem laughable to those from NY, but for an “out of town” town, it is one of the nicest places to live outside of NY. We moved here about 6 years ago and are happy we did. All the other towns mentioned (Detroit, St. Louis, etc.) are all smaller than Cleveland. Let me know if you want more information. 🙂