Brie, I feel your pain. I really do. That dysphoria is a real sneak attack. You'll be going along fine for a while, and then you get SLAMMED with a typhoon of emotions; doubts, certainties, uncertainties, high's and low's.
Even tho I am living in man mode now, I bit the bullet in 1991 and got my GRS, and never looked back. I was out there livin large for years, then went back to useless old me. Although it doesn't happen as often now that I am on HRT again, I occasionally still get strong dysphoria. My consolation is that I already made that choice. I'm not going back to being a physical male. I never wanted to live my life as a male, one way or another. That was the whole point of transitioning, HRT and GRS.
I can't count on other people to love me unconditionally. That has always lead to someone being disappointed. If they want to they can, I just don't count on it. I'd have been fine if I'd stayed alone.
If it was possible for me to live out the rest of my life as 100% Tanya, I would not hesitate, and would probably lose 99% of what is left of my dysphoria demons. But I can't have it all, and that's just the way this world is for someone of advancing years and limited money.
A couple things do prevent me from going back out tho, and that is a cis woman I fell in love with then married, and something else I won't discuss. They were big reasons, big enough to test my love and loyalty. Hopefully most of us will never have to be tested like that, but many of us have. I will probably never be able to resume my full life. I would sure love it if I could.
Make a plan now for how you want to spend the rest of your life, male or female, and then do it. Not easy, nope. Esp with the job thing. I took jobs as a waitress, driving instructor, cab driver, call center agent, trucker, and trucking is not an option anymore. I'm simply too old for it. [I'm 62]. I hate call center, but I can practice my voice on the phone. Even tho I'm seen as male there. I can't dress as I would like, but I don't need pink to be Tanya. And, really, who knows what the future holds?
Cab driving allows me to dress and talk as I wish, nobody cares. Neither job gives much in the way of pay, but that's how I continue to deal with it. Along with HRT. That is a lifesaver. I notice you're going on 2 years HRT, so keep it up. It's a major help during this time.
Transitioning is incredibly difficult; I found it was much easier alone the first time around. I am sorry to hear your wife of 33 years could not be there with you. Difficult as it is tho, that's one less hard decision you have to make. The job is your challenge now if I'm reading that right. I don't envy your position at all. But sounds like you already made your call. The hard part is implementing it.
If you complete it, you won't be sorry you did. Just don't look back. I did. Bad idea or good idea, I don't know. If I knew then what I know now... My heart goes out to you.
I hope I didn't offend you with anything I said.
Tanya
p.s. I'm in Canada too