I live in the Washington DC area and have had a pretty good go of it. Gender identity/expression is protected in DC, there are really good healthcare resources (mental health, endos, LGBT clinic, etc.), and it's a pretty progressive area in general as far as the east coast goes. I've never once felt uncomfortable being myself.
Of course, it is ridiculously expensive, and as soon as you've swapped out your summer clothes for winter clothes it's suddenly summer again. But you win some, you lose some