This is all far too stressful.
Simplify... get a nice little ultra-beamy New England-style cruising catboat with a gaff rig for low center of effort, reef when you need to, and sail flat.
You won't point super-high, but you'll make up for it by screaming on reaches and downwind without the need for spinnakers, poles, winches and all that rot
And you can sail in 2 feet of water
and run her up on the beach.
Just watch out for the boom.