Hi Scott,
I was thinking that a suitable temporary extension to the booms could be added for the purpose of extending their reach and hoisting the tender. The lift point should be 1/2 tender width + fender and a little leeway... If the mast/halyard/boom+extension can handle the load safely... and I'm quite sure all the engineers in this audience can calculate that load in their sleep! Using both masts as lift points halves the load. Tender + ~20 hp outboard + fuel tanks and gas would probably be no more than about 300 lbs.
Thanks for clearing up the rudder rotation question for me!
A short stiff attachment at the foot of the masts with ability to hydraulically raise the masts out of the hull and then do a controlled lowering/raising action would be most helpful at trailering time, but could also prove handy at low bridges on waterways. Unstepping the masts leaving halyards/nav wiring in place for transit under obstacles and raising again without a lot of fuss and bother might prove handy. As carbon masts only weigh ~150# I would think a modest set of remote hydraulic cylinders such as you might use for jaws of life type applications should prove adequate..
I'm rather trying to stimulate the collective imaginations of this group so that any bad ideas I might come up will be riddled with shot whilst I'm yet in the planning stages.
I'm told that diamond oar tumblers are rather larger large rotating cylinders filled with ball bearings, into which diamond oar is deposited and then slowly tumbled for periods of time. At completion of cycle, Large electro-magnets separate the oar from steel. Anything left that is not sand is diamond.
So please pound away. If I gain nothing more than merely contemplating the possibilities I am thoroughly enjoying myself. I find intellectual kinship with Ratty of Wind In The Willows fame, and agree with the sentiment of: "There is nothing - absolutely nothing - half so much worth doing as simply messing about in boats." by Kenneth Grahame.
/Robin