I winterize when I leave for home sometime in October, because I often won't be back again, until the Friday after Thanksgiving.
We've had some frozen pipes by Thanksgiving several times, up where my camp is. One year dad came along during turkey and after I'd winterized before leaving, he went back inside and closed the faucets for some reason? When we came back up for deer season, had to thaw several pipes that never drained completely with the faucets closed.
And the year my mom passed away (in mid Oct.), I never got back up again until early November, so the place didn't get winterized in October. Frozen pipes under sinks needed thawed and some ice in the toilet bowl, when I got to camp.
Not unusual to have temps dip into the teens/low twenties overnight there, in late October and early November.
If that happens a few nights in a row, then there are frozen pipes to deal with. Not usually enough to break anything, but enough to have to deal with, when coming back to camp.
As far as over winter problems, if no one monkeys with the faucets or outside drains after they're where they're 'sposed to be, I can winterize and come back to find no problems in the spring.
Dad closed the faucets one other time, right before we left after deer and twice my cousin has come over and closed the outside drains for some reason, after I'd left.
Both times I had broken pipes to repair in the spring, because the pipes never finished draining. The year after dad closed the faucets that last time, made him go sit in the truck before we left and told my cousin I'd have to take the drain handles off, if he couldn't let 'em alone?