Wifey B: Why?
You haven't boated in decades and she's not really interested. Doesn't sound like a recipe for success.
Get beyond the dream and what do you expect it to be like? I'd suggest you and your wife charter a couple or more boats for a week at a time and then perhaps that will give you both some clarity. Remember, one convinced against one's will, remains unconvinced still. Stole that one from hubby who stole from professor but it's so true and if you talk her into it with a hard sell or guilt, it won't last two years. She'll fly home for a couple of weeks which will turn into many more.
I love boating, love the water, but I see people like you who know nothing about living on a boat and cruising and all in involves deciding from afar it looks like a fun thing to do.
It is fun, but only if you prepare and understand what you're in for.
How do you think she, at least somewhat a non-boater, is going to like it when you take your nice coastal cruiser and cross from Turks and Caicos to the Dominican Republic and the 3' seas turn to 5' seas with short periods and you bounce around like kids in a bounce house?
One advantage we have is that not just the two of us but all those who regularly cruise with us are avid boaters and use to boating off shore and prefer calm but deal fine with adverse conditions. Charter enough that you encounter some less pleasant seas.
I want to encourage boaters, but only if it's right for them. There are many here who have zero desire to boat from the West Indies to Maine unless you're limiting the West Indies to one country of the 13, the Bahamas. Some people start out thinking of circumnavigating and end up boating happily forever after within 300 miles of home. Many in your situation are happy coming down the coast and visiting the Bahamas and returning north once a year. Still step one is get the two of you on some boats and see then how you both feel.