Great replys. One of our "Share Use" members wanted to retire to Panama and sail there, but had not sailed much. He joined for a couple years, did a lot of sailing single handed, etc. Got him prepared, he learned what features he liked and didn't like in a boat, did coastal cruising several trips, etc. Did this with no investment in the boat in case he didn't like it. You would still need experience with the mechanicals but there are plenty of sailors who would be happy to have an assistant. Keep in mind many jobs can be done from "home" and with internet access, that can be anywhere in Coastal US and beyond.
WindPath Sailing, FL