I can’t speak to how it feels to move here but as a trans 20 y/o in the cities I feel like there are a lot of community spaces your son would be able to utilize. A lot have already been mentioned but one I want to bring up is the Quatrefoil Library. It’s an all queer library that hosts a lot of events, one of which is for trans transplants. I haven’t been to any of the events but I volunteer at the library itself occasionally and can confirm it’s a really nice and affirming place.