Only thing wrong I can see is: Your sails aren't attached yet!

One question: How fast do you drive away so the knot comes loose from either the window or the mast?

Thanks to everyone.......
I'd like to try Mary's suggestion but I need to extend my tongue back towards the rear of the trailer to give the pole something to rest on. Might still modify the trailer to accomodate that since it seems rather foolproof.
Nick, I appreciate your thought process and yes, I have the Nacra. I'm not sure of the ladder in general terms just because they always seem stable in two directions but not in ALL directions. At least, that's been my experience. That's why I favor the tripod, Jeff. I think the tripod that extends upward and locks in place gives you time to see what is going to catch (shrouds etc.) and fix it AND it gets the mast raised past that point when the forces raise it and not simply put pressure on the mast ball laterally.

Raising this mast safely and easily SOLO is a real challenge for me. I won't let it beat me.

Thanks again,
Greg