I live in Calgary, Alberta -- a lot of trans ppl live here (and in Edmonton). I think part of it is because our province used to cover SRS, until our current provincial govt got into power (and it looks as if they won't be back, since they are very unpopular atm).
I've heard from several ppl that have moved here that Calgary and Edmonton are trans friendly. Alberta attracted a lot of ppl from all over because of the jobs out here -- and, so, our land scape has changed a lot in terms of how society is here as a whole. It's not as cowboy and redneck as ppl think it is. Also, a lot of ppl are apathetic out here, they really don't care much who you are. It has changed a lot in the last 10 years, and especially in the last 5 years.
It's not cheap to live out here, however. It has progressively gotten more expensive. Calgary is as expensive to live at as Vancouver; but on the flip side, getting a job out here is a lot easier than Vancouver. The recession hit our jobs hard here, but they have started to bounce back. It's easier and slightly cheaper to find a place now, but it looks like by 2011 it's going to be back to harder-to-find places, and more cost as the demand goes up.
Calgary, also, is probably one of the most American-like city in Canada. Calgary is more of a business, office, high-end type of city. We're the hub of industry and banking for Western Canada.
Edmonton is more blue-collared, and not as expensive as Calgary. It's colder than Calgary (temp wis - as calgary is usually pretty warm with mild winters; Edmonton has cold winters). It doesn't have as much growth in population, and it has a different feel to it... I have had some ppl say it feels more Canadian.
Here, there's always a Calgary vs Edmonton power play. Edmonton is the seat of government, and we're the seat of Economy.
I've only ever lived in Calgary and it's not bad. Like every city, it has its plus and minuses. It really depends on what you want and what you are looking for. People who work in business-type jobs love it here, 'cause this is where a lot of those jobs are, since we're a major hub in industry (especially oil). Some ppl say that we're a bit like Texas, and sometimes ppl call Alberta the Canadian version of Texas.
It has gotten a lot more liberal here in terms of population; but there are also old grumpies that come from here and try to get into power and then give our province a bad name -- ie Prime Minister Harper... he's from Calgary. And, like Bush is from Texas, so are the Dixie Chicks and other ppl who are form Texas and don't like him. Our current primier, Ed Stelmach, is very unpopular here (especially in Calgary). It's highly doubtful he'll win another election, and doubtful that his party will win (they won, sadly, because of apathy... then ppl cared when he started tearing up the province and crashed it into the ground).
No one really cares if you're trans here (or, I should say, the majority). People just care about hockey here. LOL
Being American-ish here, however, we also attract Bush and friends (Rice, Ann Coulter), etc, as an attractive place to visit. Other cities didn't want them, but we did. Our protests were here, but small, and not violent (which is why Calgary is often picked, 'cause no one really cares, and goes about their own business and aren't very confrontational... and if we are confrontational, it's very polite and non-violet... most, just do a groan, talk about it during coffee, then gather at home with friends to watch hockey and have a few beers. Next day, wake up and go to the office). In general, we are pretty friendly... other trans ppl from other places in the world who have moved here have said that as well; often surprised. We're more diverse than ppl think.
It's hard to explain what it's like here. o_0 Our sister city is Phoenix, Arizona and Quebec City, Quebec (in Canada). Besides sometimes being called Texas, we're also compared to Nashville. Calgary has a old-west, smaller town, but modern and global feel to it, since it's such a huge trading and international hub.
Tegan and Sara (they are indie singers, who are twin sisters and lesbian) are from here... LOL, if Harper was our Bush, then Tegan and Sara would be like our Dixie Chicks -- both from the same place, but both very different ends of the scale. Harper actually is from Calgary, just as Tegan and Sara are. So, yeah, we have both ends of the spectrum here, and everything in between.
http://en.wikipedia.org/wiki/CalgaryI don't know if it's the trans-friendliest city of them all, but I know it's not really that bad.