Throwing people out of planes isn't a long-term career and I've never heard of anyone who has gone straight from 182 meat bombing to a Q400. So pack your bags, fill the car up and hit the road NOW! If you don't know when the dry season is up north you better look up Wikipedia before you ask an experienced pilot that question, particularly a chief pilot.
Most of us grumpy old pilots never dreamed of going straight from a 182 to a Q400 without paying our dues on Aztecs, Barons, 310s, 402s and yes the much maligned by the gimme generation PA-31.
For what it's worth, I never went up north, I had a good job when I got the CPL and I made the transition to flying by doing odd flying jobs (paid) and getting known around my city. I have never flown for a company to which I applied for a job, only companies who asked me to come and work for them.