Are you looking specifically for trans folk to hang out with? If so, well, Toronto does have Sherbourne and the 519. The trans community in TO is the biggest by far in the country. Trans communities do tend to contain a lot of crazy though. Most of the people who get their life together move on and disappear.
Otherwise you get the same advice as everyone: pick something you like doing / are interested in, find a group for people who want to do / are interested in that, make friends. Friends are really just a factor of proximity and shared interests.
As for the issue of peoples' honesty etc., I dunno. You just learn to get a feel for people. And you don't let them get too close too fast. I kind of have the opposite problem really, I have such a hard time trusting people, I rarely move past the "casual friends" phase.