Hey, my husband and I just got an 18' Prindle and are bound and determined to take it out tomorrow in Sarasota Bay. We tried to put the mast up in a "dry run" tonight and had no idea how the owner's manual makes it look SO easy to just lift that thing up and in place. Can we use the winch on the trailer for some help on this? Any tips, tricks or advice you guys have on this subject?? Thanks!

Try Contacting Gulfport Yacht club up the street from you. Jennifer L. has a setup similar to the one you suggest, and I've seen it work reliably on numerous occasions - involving only one person.

hope it helps