Just Do It.
My advice for someone starting out would be to just go out and do it. As the previous poster said, it really doesn't matter where you learn to fly as long as you learn and learn well.
After you get your Commercial Multi IFR go out and get a job. Fly floats in the bush, "right seat" in a Navajo, tow gliders, crop dust, fire patrol, instruct. It doesn't matter. Go out and get the experience.
Be prepared to go where the jobs are. Admit to yourself right now that you will not find a job in Winnipeg. I grew up in Vancouver and ended up with my first job in Flin Flon. I went to school with a guy who found his first job in St. John's, I met a guy in St. John's who found his first job in La Ronge.
You get my point.
As far as the industry goes, I haven't got chrystal balls. I have no idea where it will be in 5 years let alone 10. There is turbulence now, it will probablly smooth out in a year or so. This industry is notoriously cyclical. The best time to train is in the down cycle, so you are ready for the upturn in my opinion.
Good luck from a guy in the middle looking at the backside of his career. I'm having a blast now just as I did in that 185F in Flin Flon.
One other piece of advice. Enjoy yourself! Take the time to look around where ever you are in this business and enjoy your accomplishment of the time. You'll find yourself chasing airplanes and jobs, so slow down. You'll need the first job, then you'll need twin time, then turbine time, then turbine command, then you'll need jet time, then heavy jet, then intercontinental experience.... You get my drift. I've known guys that just couldn't wait for the next step.
Again, good luck!