Welcome to A) the West Coast, B) Trans-friendly C) and a great place to live. As to where to live, Gresham/ Troutdale is nice ( on the east side ). We do get windy at times. Yes I live in the area. Clackamas is nice. Can be too country for my taste. Downtown is really nice. A lot of the gay community lives downtown. Washington County is nice, but can be a little spendy.
Stay out of southwest Portland. It is called "Felony Flats" for a reason.
We have a good therapist here and a Trans Doctor. But you would have to see if they are taking on new patients.
I love Portland. Pride week, several clubs ( downtown ). Lot of shopping downtown too. Out here in East County, as we are called, is nice. Quiet. Not much gang activity. Thank the Gods.
A couple of us live in and around Portland. It seems that Portland is to the Trans community, as San Fran is to the gay community.
Oh and remember to "Keep Portland Weird !".