Re: A bluewater live-aboard for under $20k
The Albin and the CDs are probably the meet the 'rugged' requirement, both are proven voyagers but neither may get along with your 6'3" frame.
As ever, you have some contradictory requirements - size vs budget vs capability - but most any well found boat can island hop in the Caribbean given time to pick weather windows. The tricky part is actually getting there from the East coast USA.
Ideally you'd find a suitable candidate already there when you're ready to cruise.. but that would preclude your 'getting to know her' at home first...
As Donna says, best of luck!
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)
1984 Fast/Nicholson 345 "FastForward"