With the current state of hiring in these parts, here is my advice (and my first post here too):
1. Work permit for pilots - forget it. Just not going to happen. Any outfit wanting to hire you, will need to prove beyond any doubt there are no Canadian citizens/permanent residents available to do the work.
2. Building time over in these parts is a tough road to hoe if you're older, and need to delve into the savings to cover the difference between your needs and the pennies you'll make - even somewhere like FlightExec does not pay well, and you need good experience to even get near a Cheyenne. The getting into Canada on a work permit would stop you anyway, unless you have another route into the country to get your IMM 1000 (
PR Status).
3. Takes 5-6 years after professional license award to build the hours from the ground-up to get a decent ride, generally.
I don't mean to put anyone off, but it is one of toughest countries to get into the business and stay there...
Beacher