What is weird for me about those 250 Multi time position, usually people who have those hours are already working somewhere, so it means they are expecting people to leave their current place.. Maybe for direct entry captains, but why would a First Officer do that?
You've hit the nail on the head about the baffling requirements of Contrails without ever reading about it. Contrails is not an air operator requirement per se, it is a requirement that some resource companies use for insurance purposes that air operators are forced to follow. If you don't want to follow Contrails, then you don't get their business. The requirements are often so high that in a pilot shortage, you can't keep a hold of pilots long enough that they build their experience to meet those requirements - well, at least without using all the different reductions and lets built into the system. Most air operators would do away with Contrails tomorrow if they could.
The thing to know about Contrails is it was constructed following a series of accidents and at a time when pilots here needed 3,000 hours to fly right seat in a Navajo, 5,000 to fly right seat in a Dash, and 10,000 to fly right seat of a 737. In the way back days, pilots spent a lot more time instructing than they do now. "Short" then meant instructing for 3 to 5 years. Now it's 3 to 5 months. The requirements were set for those times as pilots had nowhere to go for years on end, meaning a new hire pilot often didn't have a problem meeting Contrails requirements, or if they did, they were short by a dozen hours or so, not hundreds. Now that you can get on with Jazz and Encore with 750 hours or so, Contrails seems archaic, but it's been around for so long, and downturns happen frequently enough that the pain of an upturn is short lived, so Contrails will not be going anywhere anytime soon. The guy who developed the Contrail requirements laughed all the way to the bank, and most of us who worked under the system wished we had come up with the idea ourselves, if only for the millions earned on the contracting fees alone.
As for getting a job up north for your wife, don't be so sure. At least, look into it. I'll admit that things may have changed drastically since I left Yellowknife, but when I left I had friends teaching in the school system who did not have a teaching degree, and some working good paying jobs in the trucking and mining companies who only had a high school degree. Heck, my wife was earning $80k with a catering company and she had no Canadian schooling credentials to her name. But, that was 15 years ago, so it's likely changed a lot. But still worth some looking into.
Yes, the ramp work sucks, especially if things drag on. I spent a year working the ramp and got lucky getting onto an airplane after a year. Guys my age who made it to Yellowknife before me worked on the ramp for up to 5 years. When I left, guys were spending 6 months or less on the ramp, or were checked out almost immediately but did a 50/50 split ramp and flying. Regardless, while I don't agree with the whole "pilot-in-waiting" structure, almost anyone with a brain gets a type rating and commercial experience out of it. And, if the industry has a downturn, you've at least got your foot in the door for the next upswing. That can be worth more than hours in a logbook, especially when the recruiter looking at your resume recognizes a company on your resume. But it can be a hard go, and I didn't do the north with kids. That's a whole other factor to consider, which sounds like you are.