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I used to work in the city and now live/work in CT. I grew tired of it. A large factor was the housing cost anywhere within a decent commute time of the city. So naturally, I wouldn't call you crazy!
If you were to make such a move, I would stay away from working/living in Fairfield County since that is a NYC bedroom community. You get all of the traffic and headaches that go along with the city commute, so if you are going to be in that area, you may as well stay put.
If you have an opportunity in another area of CT, I say go for it. New Haven is a great city and has nice surrounding towns as well. If you work out of Hartford, there is some decent priced housing in many towns, from bustling small cities to more quiet/rural areas. So far the greater Hartford area hasn't become too unaffordable for regular middle class people just yet.
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