First, I meant no offense. Just a basic question - more lifestyle than aircraft size. Personally, I would not be happy if I were getting bumped off the Caribbean flying on the 757. I agree that there is a big difference between flying 2 long 757 sectors (i.e., Toronto - Los Cabos and back) and flying 6 Q400 sectors or 5 CRJ sectors in one day. Regional flying can be just as exhausting in my opinion (and quite boring if you fly the same routes every day) as longhaul flying. Six sectors in harsh winter conditions with all of the delays does not seem so appealing.
But that is just my opinion - yours might differ.
By the way, in my recent travels to the Middle East, I met many Canadians. I just met an Air Transat A310 pilot who was on his way to an interview with Emirates - so, my suggestion about flying in the Middle East is not too far off. Plus, with 757 time, at least the Jazz guys would get noticed by EK - although CRJ-900 time might get them an interview at Qatar but an interview with EK is almost a guarantee with decent 757 experience. Not sure if just Q400 time would get you an interview at QR - probably not likely at EK for those who might be interested in other options.