As an old person I feel some responsibility to your generation.
Buying a house in Connecticut in 2018 comes with a negative expected value.
Unless you’ve got a spouse and kids combined with two solid well paying jobs do not invest in a house in Connecticut.
If you’ve got a spouse and children buy in a top 15 school system, that will limit your losses and you’ll get some ROI from the schools.
If you aren’t married and aren’t making incredible money get the hell out of here.
There will be a time when the market in CT comes back. I think most young people would be wise to wait for signs of life in the CT economy before buying a house. We are near the end of this economic cycle (a good cycle even though Ct isn’t seeing the prosperity). During the next recession, the CT market should get even worse. That will be the time to buy. I am hopeful that as CT continues to work through the economic messes that face it, there will be light at the end of the tunnel in 4-7 years. For now, I think this kid should rent. There is just no benefit to buying a house in CT that you don’t want to live in for many years.
If I was buying in the 250k range up there I’d look for an updated , older farmhouse or cottage type home 0n 1 or more acres in a place like Ellington, Somers, Suffield, Portland, East Hampton, Marlborough, East Granby/Granby, Barkhamsted etc. Those houses will always have some appeal for the land and character. I’d plan on enjoying my house and land but not the bar and restaurant scene in town. You’d have to drive 15-20 minutes for a lot of options but each town usually has a few spots for drinks/food and watching a game. Build a firepit, join a softball league, play in the town men’s basketball league, golf, fish etc. If you make it big, all of those towns have beautiful, more expensive homes to upgrade to.
Otherwise, rent and live where the action is. Do not buy an ugly shoe box in an ugly town. That’s how a lifetime of living in an ugly shoebox in an ugly town begins.