Pulling out to a mooring sounds like an excellent idea if you can not raise your main on the beach. If you can use the same setup when returning, it sounds like a great idea to land under complete control.

I only roll from the top downwards if I am to ship a sail. Otherwise, I roll from the bottom up and put it in the trailer ready for the next sail. Of course, we use the sails two to three times a week and dont move the trailer as we have mast-up storage at the club.