As a former Cleveland resident, I’m convinced that the winter driving skill set for many folks does a full reset to zero each year.
So until they’ve experienced multiple days of slippery roads in a winter season, the wreckin’ is rampant.
I used to think that, too.
But perhaps there's ANOTHER explanation:
Usually, the first few snows fall on pavement whose underlayment (the first foot or two of roadbed) has not yet frozen. The unfrozen roadbed busily thaws the fallen snow on top of the cold pavement, which is exposed to the freezing temperatures.
You're more likely to end up with a thin glaze of ice under those conditions, whereas later in the season, the falling snow stays cold, and doesn't melt, providing better traction. I have a buddy whose commercial dump truck becomes absolutely undriveable in such conditions - he explained the mechanics of it.
Once the roadbed freezes a month or two into winter, he's good to go.