Cheers guys! I'm glad I took a year to think this through and explore, and I'm about ready to start with more permanent changes with T and name change.
I'll likely decide over this weekend whether the trip overseas is happening, when I make a budget and get a couple more details. If I do this, it'll be from mid-June for a couple of weeks. I'm a bit nervous about what it's like traveling with T. I'm also nervous if I do have some early success with T in the first couple of months, and how that would be perceived by my traditional family abroad, particularly my Dad. Actually, one of the other things I've wondered about, but not done a lot of research on, is that I'm a dual national, and I wonder what I would have to do to also switch over all that ID. More of a PITA than in Canada, for sure.
My work probation period will be over by early July, but there are protections here for trans people in legislation and at the office. I did apply for a more senior role but I haven't heard back yet if I've made the shortlist.
Anyway, the debate is more or less starting in late April/May vs July.