I may be showing my biases (I know I am) but I would really recommend looking at cars that haven't spent any time in the North East. They just look better. They haven't had to deal with marginal roads with pot holes and the weather. Take your own test. Look at an 8 year old car that has lived in NY and one that has lived in the South West. The differences in the paint, the rubber moldings, the wheels and the underside are everywhere.
If it was me, I'd plan a long weekend to Texas (Dallas seems to have a lot of them) and plan a drive back. I happen to enjoy these cross country drives, but if you don't, most dealers and brokers are happy to ship and it will (only) set you back around $1000. A thousand that can disappear quickly trying to bring a Connecticut car back up to snuff. I like a broker in that area at eCarhouse(dot)com because he finds nicer cars than I can find and he charges wholesale KBB. Hard to beat but I'm sure there are other top notch brokers too.
You won't regret it. Good luck.

 

That is a good point, and you are correct. Not only will a car from the southern regions of the country be in better shape (for the most part, dont forget about our friend the sun), but it would make it easier to find the car I am looking for if I expanded my search area.

But, its hard for me to take the chance of flying across the country and having the car not meet my expectations/ being inaccurately described when I get there.

I'd be a lot less disappointed if I drove 4 hours to see a car rather than fly from NY to LA lol.