the points you stated were all good and i agree with maintaining insurance over the winter. but ill clearify one part for you. the claim for a customers property damage goes off of the insuance you had at the time you did the work. You could do a job today, drop insurance tommorow and two years down the road if there is a claim, your insurance company you had yesterday would be the one responsible. We saw this a couple years ago when we switched carriers, we had a claim from an earier job when we had a different cariier. The old carrier was the one we filed the claim with not our carrier we were currently using.
In other word's "don't drop your insurance" That insurance company will hold it against you. Have you ever heard of insurance point's, this is how they score you when you drop insurance. And they might not reinstate you. It's not fair but that's the way it is. But i'll bet they will restructure your payment's to make it easier to get through the winter.