What finally convinced me to lower it slightly was realizing that winter damage usually isn’t from one big freeze, it’s from weeks of small freeze–thaw cycles. When the water sits right at the skimmer mouth, every thaw lets a little water creep in, and every refreeze pushes on the plastic again. You don’t notice anything wrong until spring, when there’s suddenly a crack or a slow leak.
Dropping the level just enough to keep the skimmer throat dry breaks that cycle. Even if you’re plugging and blowing out properly, the air gap gives you insurance if the water level rises later from rain or snow melt. You’re not draining the pool, just removing the skimmer from the stress equation.
Plenty of people get away with leaving it full and plugging, especially in milder climates. But for a first close, lowering it a few inches below the skimmer plus plugging the lines is the most forgiving setup. It gives you room for winter surprises you can’t really control once the cover is on.