I’m on a lake in Maine as well, with my Scot moored just offshore. Where are you located?
To your question: Rolling the sail is best for the sail. You can find older posts here on the forum that describe how to do that. I sail solo all the time and find any way of dealing with the main a chore. I roll it the best I can alone and sail tie it to the boom. Then cover it all with a tent mooring cover. If you have a crew to help it should happen easily.
Marty