I'm from Toronto so I guess I'll answer.
As far as how trans people are treated by public/government. At least here in Toronto it's not totally uncommon for me to hear transphobic comments on public transit. As far as in most social circumstances, depends where you go. There's definitely a base queer/trans positive community here, so there is support. As far as job discrimination, it depends on the job. Obviously you're going to find less discrimination in an office job than at a minimum wage or manual labour job. At my university (UofT) they have measures in place to accommodate trans people. You're allowed to change your name and sex marker on university records without having done so legally. There are a growing number of gender neutral washrooms, and there are lots of resources for trans people. Resources outside the university, there are two main places which are Sherbourne Health Clinic and the 519, both of which are right near the downtown core. Especially since there are also a few more queer/trans positive spaces in the downtown area now, gender neutral washrooms are more common now. There's also quite a bit in the way of trans events so you can meet people etc. Access to OHIP for any kind of SRS/top surgery requires you get citizenship first, afaik, but if you have the money yourself you can get it on the spot without any letters.
Legal protections, right now in most major cities the legal systems understands trans people as protected from discrimination under the sex category. That isn't really a reflection of reality, though, especially for trans people living in low-income situations or who are poc or living with a disability. That's similar everywhere and I guess if you're going to compare us to other nations we may be slightly "better" when it comes to trans rights, whatever that means. There are bills going through both Ontario provincial gov't and federal gov't (Toby's Bill and Bill C-279 previously Bill C-389) to try to add gender expression and identity to the human rights code and criminal code, but activists have been trying to do that for years so...
Honestly, if you're already someone with a lot of social privilege (aka white straight middle class able-bodied etc.) where you live then it's going to be the same here, versus a trans person who has to deal with racism, classism and/or ableism every day is obviously going to come up against more transphobia and discrimination.
For T university benefits and work benefits will cover it (depending if you're part-time or full-time), though for work benefits it depends on the work place. Most places will, afaik, though.
If you're going to move to Canada and are trans, honestly Toronto or Montreal are probably the best places. If you're only an anglophone then stick with Toronto. I'd steer clear of Alberta and most of the West entirely as they tend to be a lot more conservative. Even Vancouver which is pretty progressive, afaik doesn't have as many resources as Toronto/GTA.
