"I'm not sure if I want to keep flying till I'm 50 and since I'm 33 now,"
In most professions (other than sports and....) you only REALLY start to make a decent living after you're 40. I think it's even more so in the airline business. You have said (and you sound) happy in your current job and it sounds like there is a good chance of advancement. Why only think of flying to age 50??
Also, what we don't know, and don't need to know, is why you want a Canadian passport. You have to balance the long term opportunities that Canada MAY give to you and your family with your current and future health & happiness. Not all immigrants succeed, and for many it's a whole generation of slogging away at boring jobs which you are grossly over qualified for. Then your kids get their chance. There's no simple answer, it all depends on your individual circumstances.
+TSRA has some good advice - and I'd also suggest that until things improve with the US/Canadian relationship, investment/expansion in any Canadian business will be, at best, muted