Looked at Canada a few years back. Getting a residence/right to work permit should be fairly easy if you are a college educated airline pilot and are a native English (or French) speaker. I think there is a financial requirement, along the lines of $10,000-$15,000 (Canadian) that has to be placed in a Canadian account. You'll have to look up the specifics, but I know I met all the requirements back in 2010 and what I mentioned were the biggies that I remember.

I went so far as to get a Canadian license as well. The process is pretty easy. As mentioned get a Canadian medical first. I got lucky in that my AME in PHX was also a Canadian AME. Once that is done they will send you your medical with your Canadian "file number" printed on it. The file number will be what is used to identify you for everything else in the process; it also becomes you license number. You then fill out a form that gives TCCA the right to request your records from the FAA. After TCCA gets your FAA records you then can schedule your conversion written test (25 or 30 questions - can't remember). There is a flight school in Winnepeg that has an online study course for the conversion test. I paid $100 (IIRC) and spent three days studying for the test. Head up to Canada and get some passport pictures taken and then take the test. The test took me 15 minutes at the TCCA office in Vancouver (the one on Burrard Street in downtown). I left the TCCA with my logbooks as they needed something to prove you met their ATPL minimums. Used a credit card to pay for the test, license and $30 for each type rating I wanted to transfer over. About two months after I took the test I got my Canadian ATPL in the mail. It looks like a passport complete with a passport photo identification page. You can pay to have your logbooks FedEx'd back or you have to go pick them up.

I have not pursued Canada yet, but as long as I send TCCA copies of my PCs and keep my medical somewhat current, I have my license ready to go. The other nice thing is if I ever run afoul of the FAA, I have another ICAO license with which to make a living in the contract world.

All told I spend about $400 on the conversion process.