If you are serious start IMMEDIATELY saving every dime you can, after first paying off debt. You can not have too much $$, so become the most frugal you an be while exploring the lifestyle.
In that regard, your library is your new best friend. Read every book you can about life aboard (but none about surviving the savage sea -- the shipwreck books
are not going to tell you what life out here is really like)
Blogs and books
can keep the interest building while you downsize your possessions. Everyone has too many/much so if you're not LOVING your stuff now would be a good time to begin to downsize.
My starter advice in a nutshell:
#1) Pay off all debt
#2) Save every dime you can/cutting all extraneous expenses
#3) Read, read, read
#4) If you are honestly thinking this life can be what you desire, then begin to divest yourself of the accumulated junk that won't fit aboard your boat.
Quite frankly, having little is so freeing, that even if you chose not to become a boater, you'll probably like it. Stuff is just stuff -- burdensome at worst and if it's not bringing you pleasure, this is your opportunity to become less materialistic/in the hunter
gatherer frame at least.
Please understand I do have all my stuff aboard, but only the best of, versus every blessed thing I managed to accumulate over the years. For instance, I have silk floss (but none of the cottons) ...
Like most folks (everyone?) you probably have quite a collection of shirts, but most likely only wear a half-dozen or so on a rotating basis. So, now is the time to get rid of the extras (donate to your favorite charity)
Anyway, I do wish you well. It is fun out here -- but as you must have seen over the 8 months you spent in the Carib, it's not all wonderful. People make the difference, and if your wife is on-board with you, it can be a blast.