I know there is a certain Macho component to being j30 skipper ... but a lot of this could be easier if you could borrow a sock.
or maybe raise it with breakable stops
Will you really need a Pole? or maybe think about using the spin somewhat more like a cruising spin?
I think the key will be going as simple as you can. and don't think like its a J30 racing team ...
Not able to use an autohelm is a big handicap single handed on a J30.
going down wind with any kind of sea state boat motion ... rounding up or jibing ... controling the boat on a broad reach
I would try to get a crew person on board for the practice ... just so you would have more time to test alternatives.
I would love to be on a spectator boat to see how you do it.
