In the land of ice snow, also known as Edmonton, I don't dare strip the snows off before well into April. This week we got 40cm of snow and before that we had days of freezing rain.
Depends on where you live and how important it is that you be able to move in the snow. My wife is a teacher and MUST be at work, regardless of weather/roads. Schools here never close. Ever. So, her Subie OBW has it's snows on a little later than many folks, and they go on fairly early. If they wear faster, oh well. At $500 or so a set, it's not a big deal in the overall operating of the car.
Me? If either the C230 or the Forester has snows on it, I'm okay. Heck, even if they both were on summers, I rarely HAVE to be anywhere, so I might just stay home.
With all the new snow, I spent an afternoon climbing the snow-plow berms in the neighbourhood with the Forester. If it didn't make for such a brutal commute for my wife, I wouldn't mind the snow!