I'd think so; as others have mentioned, the cost of living issue is significant. In the city itself, I'd expect the most LGBT-friendly areas to be Jamaica Plain, Roslindale, the South End (haha $), and Allston-Brighton. For other areas, there's probably a pretty good correlation between the bluest parts of this map and where you'd feel most comfortable (sort by Biden %, the top thirty communities should be pretty good).

I think there's an incredibly low chance MA will, at a state level, diminish protections for trans people. Quite the opposite, now that we've finally got a Democratic trifecta (complete with lesbian governor--you can come complain that she's too cozy with finance and developers, maybe...).

Boston is one of the safest cities in the country overall. (Weirdly, NYC is doing even better on the violent crime.)

Right now? Can you find a place you can afford? If so, come on up.

Also: I glanced at your post history. Feel free to chat me if you want synagogue rec's.

/r/Boston may give you additional thoughts; its also a very active community.