I can get into more details later because I'm short on time, but I think your "fear" of having a TC license and applying to the ME are unfounded. There are a ton of American and Canadian pilots flying in the Middle East. Maybe one of them will see this thread and chime in.
My question to you is this: Why do you think going EASA and spending 2-3 years toiling as a FI will get you to the ME that much quicker than staying in Canada and getting a Twin job? I'm no hiring manager, but it seems to me flying B200s around the North is a lot more conducive to a ME pilot than dicking around in a C150 in Europe for 3 years. Without citizenship in the EU your quickest route to the ME, if that's what you want, is (barring some loophole) to stay in Canada and work your way up.
Face it, you're going to have to work your way up no matter what. Even guys going the CTC/Oxford route aren't guaranteed jobs and many are left disappointed. Sure, have the dream of flying a 777 for Emirates, but don't fool yourself - getting an EASA license won't get you there immediately. Realistically the timelines will be the same Canada vs. Europe. In your shoes, Canada would be quicker due to the VISA issue.
Keep in mind I'm only half way through my PPL so take my opinion for what it's worth - not a lot - but I've spent the better part of a decade thinking, talking with others, on these sort of things, if that means anything
