RE: Searching for the 'Perfect' Loop Boat...
WE purchased and outfitted LUCY specially as a loop boat.
Tho were sailors at heart the concept of running 50++ locks in a 33 ft boat with a 50 ft mast on deck was not considered as a "fun trip".
LUCY is a 50 ft US Navy Utility, with a lobster boat deck house.
Set up to cruise 2 it has only what we need.
I lived aboard (working years) for 22+ years and so avoid docks and prefer the hook.
A huge commercial rub rail , and a robust mid-ship cleat (P&S) and a hyd windlass was installed.
As was a Robertson commercial grade auto pilot.
Propane range with oven and propane fridge freezer allows unlimited time with no noisemaker , or dead batts. Dickinson oil range for cool days.
For the Canadians we installed a waste tank and pump out setup.
For out of service time a 75W solar with charge controller keeps up the batt set.
Total investment about $50K .
Of course some folks would question a 50 ft boat set up for 2 , but they haven't been on the huge couch in the PH , or under the 10x10 awning on a 15 ft after deck.
Sorry ,no acres of teak