Need advice on Maine to Bermuda Run.
I did the trip in O''day 37 from Annapolis to Beaufort N.C. There are some nice stops on the IC well worth the trip. Leave from Beaufort. You will hook you up with many boats heading out and a degree of safety in numbers. Have you considered the Carib 1500 Rally concept?
If you have original rig with swaged fittings think of re-rig. Blowing a sail is one thing, collapsing the stick is un-thinkable.
May is a bit early from Beaufort. You might hang out and wait for company. Is do-able SSB is degree of safety, life raft is no fun.