Newbie to this forum

[Olddawgsrule]

I'm reading, searching and learning.
I know this has been asked several times before, yet here it comes again..

I'm convinced, unless very lucky, whatever the used I buy, double it to make it sea-worthy.. Okay, ready.

The real question comes to costs of living aboard vs. land.
I'm in the mind set that it's pretty even. Actually thinking higher aboard.

Retirement time is here!
I'd love to winter somewhere warmer (live in the Northeast US).

Sure I could buy a condo, but I'd hate it...
I need to travel.

I have a couple areas in mind I think could suit the need, but reality sets in on what the 'real' costs are to dry dock the boat while not there, slip costs, you know, all those incidental costs no one looks at.

My two places right now are Dominican or Puerto Rico.
Puerto Rico has the winning hand so far for sailing reasons, Dominican for price..

Suggest as you may.
Steer me into the right threads to read.
All suggestions, if friendly, are welcomed.
Remember, I'm a Newbie...