My 19 year old son is a freshman Mech. Eng. student at the Univ of Texas at Austin. He had his Statics exam on Thursday, and I took him out to dinner last night, where I presented him with this problem. We discussed it for the whole meal, drawing with crayons on the back of the kid's menu.
After looking at his results, we agreed that we would redesign. I like Bruce's I-beam idea, myself, but what we decided was that the post should be fixed, and the davit pieces should swivel around the post with a collar, hinge, or other means. We also brought the winch in, right next to the post, and made it pull up a platform with a wheeled carriage riding on the post, something like a dumbwaiter. We didn't see the need to hang the winch so far out from the post.
We also came up with the gate idea so that the platform only would come up to the level of the deck rather than trying to go over the railing - this would make it a lot easier to unload as well. Of course, my son immediately saw the possibilities of making this platform a people lift, which I told him had already been vetoed by the professionals here...
Anyway, it was interesting to him, as the previously mentioned ME undergrad...