Two roads diverged in a yellow wood...

[curtisv]

I learned that traveling via sailboat isn't like in the movies, and you'll likely end up motoring most of the time. Bareboat charters will likely be our path,
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I'd stay the course on the reaching financial independence goal and then assess what motive you guys as long as it involves so form of sailing:)

Not sure what movies you watch or where you are sailing that you are motoring most of the time.  I can safely say that I don't do much motoring.  I don't have a motor.  A big difference is lake or inland sailing vs coastal sailing.  The ICW is inland and much of it you have to motor if that is something you'd consider doing.  Winds are also generally lighter on the east coast as you go south and a lot more dead or 2-3 knots once you hit Florida.  For most of New England coastal sailing thar be wind.

Bareboating gets expensive.  Depending on size starting around $3,500 to $5,000 per week (and up) in the Caribbean last I checked (a long time ago) with the smallest charter usually being 36 foot.  Shared among two couples only half as bad but there is airfare and other expenses.  If only now and then its not too pricey.  I know someone who keeps a boat in St. Martin and takes 2-3 months off each winter to sail.  Storage costs about $2,000 when he's not there but maintenance can be pricey.  He has a C&C 34 up here he got for free (needed major work, insurance total) and the boat in St. Martin was also a fixer upper but his line of work is boat fiberglass and painting.  I don't know if he headed south this year.  Last season he barely made it back before travel restrictions would have kept him out of the US.

As to renting a trawler, keep the fuel costs in mind.  A friend of my sister lives on a 58' trawler and she and her husband never go anywhere, spending 2-3 months at a time or whatever the tourist visa allows so as not to use fuel moving.  Just the fuel needed to run the genset is costly.  Thats a big boat so a substantial move can run thousands of dollars.  Last I heard they were getting out of Venezualla to avoid the political chaos but I don't know where they went from there.  Covid has made it even more difficult.  They have lived aboard for 15 years or so I think.

I do agree that financial independence needs to be the first goal.  If you don't have high ongoing boat expenses like storage fees, then maybe hang onto the boat, retire, get settled into a budget, then decide what boating expenses you can handle.

Curtis