A few weeks twice a year is for me the key detail.
IMO really makes no sense to buy a boat and not be able to use her for 90% of the year. especially when you factor in the cost, time and aggro to maintain a boat - even when you use other people. The boat being away from you means could easily find your vacations being centred around boat maintanence!
I would suggest a triple track approach:-
- sign up for a training course in the Carribean, a bit of a working holiday but they won't be learning
you 24/7 (wouldn't get many punters with that approach!). Starting from zero you will learn a lot quickly that would take you a lot longer to puzzle out yourself, albeit nothing about boats is rocket science - but life a lot simpler and easier when you can at least get a handle on your unknowns / where you need more experiance or to get more confidence.
in the Carribean, either on own / with freinds or family
or even try and get in someone else's boat charter!
- Not sure if you are still landlocked, but if not (whether sea or lake) then either get some more sailing time in locally, paid for, for free (add beer!) or (IMO ideally) on own boat (no matter what the size, but at your (and my!) age I would suggest at least 17-20 foot as something that won't tip you into the oggin as part of the nornal "fun"!.....will learn a lot from sailing on other peoples boat (from the variation in approaches - and the don'ts as well as the dos!), but no subtitute for also having own boat (Ownership a different experiance from being Skipper
from being Crew).
The above should keep you going for a year or 3 which would place you a squillion percent more in a better position to decide whether owning a boat abroad is actually as wise (for you) as it is attractive sounding!
Even if the answer is then no, could also explore buying
a boat in a Charter
program (the company uses it to rent and you get weeks a year to use, and after 5(?) you get to keep her - it don't work as a true investment, but it does work for some - plenty of threads on CF about this). Or fractional ownership
/ syndicate share the boat and the bills!......yer never know, by the end of all that might end up being able to spend far longer aboard / away from home, in which case it is..........game on!