To the OP, sounds like that you are on top of the food chain here in Canada. And as you have indicated, waiting for the payoff down the road appears to be frustrating.
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I've said this before on this forum, going expat involves a hell of alot more than just changing jobs. You are changing your life wholesale from A to Z. So sit back and think what is best for you, as in, living in the sandbox or Asia for an extended decades long period, or forever, or, a bit less money in your pocket for the current lifestyle. The grass is not as green on the other side as you may think.
I need to laugh at those who invoked Jetster Vietnem as a better place to be. They pay a total of about 11000 or 14000 US per month for a captain, something like that (I got an email from a headhunter) and that includes everything including your per diems. You will also not have the same living conditions as you would have in North America, I know becasue I did in fact do a Vietnam Airlines contract for 4 years. You might want to look at airline pilot central.com to see where an air canada driver in the same plane makes, and factoring in taxes, you are much better off in Canada, once you get that slot which I hear is not all that difficult to get anymore. You are not as well off as the US, they pay much more. So go US if you can, right to work and all.
Think before you jump; typically people of my generation went expat because we had zero choice after all of the bankruptcies, downsizings, and mass layoffs. It's not like that anymore, things are booming, and, it is only a matter of time, and a short couple of years, if that, that you will be into the big bucks and on easy street, without all of the upheaval.
Attempting to understand the world. I have not succeeded.
veni, vidi,...... vici non fecit.