I think you may be looking at this from the wrong perspective. You are concentrating on choosing and buying a boat
, but what you are really doing is buying
a lifestyle. Boats, you have some training
and experience in. The lifestyle, not so much. And aside from the details, a lot of the boats you're looking at are really not that different from each other.
I think you should consider shopping
instead for the right people to buy a boat
from. Choose a couple/family like yourselves who have been (and currently ARE) living this lifestyle on a good boat that is well equipped and thoroughly sorted. A boat that is expertly rigged and maintained and in daily use by people more experienced and knowledgable than yourselves who are either up/down sizing or moving ashore. A boat that is a turn key, sail away cruising system that you can literally step into, and with a day or so of instruction and familiarization from the sellers, sail off in.
They will have already dealt with all the issues and questions you will have and some you never thought of, because how would you know?
Admittedly, this will be a lot harder than clicking through hundreds of online listings of boats tied to docks in various parts
of the world. But there are a considerable number of family
cruisers who take a year or two at some opportune time of life to go cruising. Buying
a fully sorted cruising machine from someone like that might put you months and dollars ahead.