Ditch your "friend" he's not knowledgeable and is feeding you bad advice on nearly every point you've raised here.

Contrary to misconceptions and perceptions the boat does not sit on the stands it sits mostly on the keel and the stands simply balance it. Thousands and thousands of boats are stored mast up and very, very few actually ever tip over. My yard has never had a topple over and about half the sailboats are stored mast up..