My folks moved from PA to CT for family and work.
I consider CT a great place to live and be an outdoorsman and I'm glad I was educated in CT public schools.

The cost of living is high no doubt but what really kills you is property taxes and other state taxes and fees. It could be hard to retire here in a large home in some towns.

The Carolinas, Florida and Texas have ridiculously low property taxes and home prices. I'm 43 so I've been formulating ideas for retirement and right now one idea I like is to buy a three family home in CT and rent out two floors to pay the mortgage and taxes and keep the 3rd floor as my CT summer home. Alternatively I might buy a tidy little cabin in upstate NY or Maine near a lake and some nice rivers and live there during the summer and rent it out to hunters, snowmobilers, skiiers etc...during the winter months when I'm not there.

To avoid the cold winters and dealing wtih snow when I'm older I'd buy a small home or cabin or cottage in North Carolina and keep a 20 foot fiberglass boat down there if I were near the shore. If you go on line and check out the listings in NC you can see how inexpensive homes and property taxes are.

I've been doing the research and right now anyone can easily buy a nice place in various parts of NC for around $70,000 to $85,000. Same is true in upstate NY or ME...you can buy a nice cabin on a small piece of land for under $100,000. So you can buy a place in the south and a place in the north for about what you'd pay to have one nice place in CT.

It's only 3.5 hours from upstate NY to CT if I want to visit with my family and hotel rooms are $85 bucks per night!!!!!!!