Keep in mind that we are on the shore of Lake Erie, there is nothing line of sight from my mast head to the great white north of Canada, so yes it can get quite windy. That said, any given year has a different percentage of boats stored with the masts up. This year so far every sailboat out but one Hunter 25.5 has the mast up. The club is run by the members so there would be no formal recommendation by the lift crew unless they felt I was doing something that would be a safety issue.
The boat is a 2008 Hunter 27-3, 5' draft, 7700lbs. dry. We all store on stands, no cradles.