Should I wait until next winter to go to truck driving school? Is it just a sales pitch to get somone to go when schools have low numbers of students? If I start now I will learn how to "feel" the truck when it is driving. That Way I can control the truck easier next winter? That is what an older truck driver told me. And yes, I already have all my learners permits, and have applied for the dangerous goods background investigation. If I don't go then I can show an employer that. He will be impressed that it is more than he can check.
What I was told by several employers while I was in CDL school is that you need to go to CDL school when you want a job. After 30-90, many employers consider your CDL school experience to be too long ago and will insist on a refresher course (more money out of pocket for trucker school). So, if you want to drive next winter, then you should go to school next winter. I actually wanted to start working this summer and was talked into a "winter" CDL class (then we got record high temps in Michigan and I melted in the yard, instead of getting winter driving experience).
I say go when you have the opportunity. You live up north, you'll get plenty experience depending on what kind of what work you do.
It preferably you go now and get the basics down while the weather is good. Then advance to winter driving when you have a few miles under your belt. You're gonna be sweating bullets for the first month or two. Get that out of your system on dry roads.