Buying a car or transporting a Subaru to Puerto Rico?

Really in a Car Buying Quandary...  Please read and advise... 

OK so here is my situation. 
I am close to retiring to Puerto Rico SOON.  I looked into what would be the perfect car given the terrain and fuel economy.  I considered the Chevy Equinox, Honda CRV, Toyota Rav4 but the car that stands above all is the Subaru Forester.  I did extensive research...  Good Mileage & Reliability for a MINI/Cross SUV.
Anyhow, I understand there is only one "Official" dealership that deals directly with Subaru(s).  Trebol Motors in San Juan-Santurce.  (I realize service may become costly, particularly for parts).  A "used" 2009-20011 Forester is what I'm considering.  My dilemma is either transporting from NY to PR or buying from some dealer, on the island. 
My fear is the tax fees to ship, even more so if the vehicle is considered rare. (Subaru). 
If I go on "Clasificados online", I saw several Dealers (& some Private Owners) have "used" Subaru "Foresters" for sale.  Given costly shipping disadvantages, I probably will check out Trebol Motors and/or others advertising on this site.  I don't know any other website in Puerto Rico that sells cars on line (other than private dealers, Craigslist or some auction)
*I will not fully retire to Puerto Rico (just yet), but travel several months at a time, starting next month through 2019/20.  By then I should have all my affairs in order before staying for good in PR.  Buying a (used) car will save me over renting several months at a time... 

Now that you know my history...  Here are my relevant Questions...

1. Is there a Carfax or similar for vehicles in Puerto Rico?  If not, I might just buy a Subaru here and ship.  I get conflicting info I've read online; a "Carfax"Plus" or something similar seems to be in existence but...  Anyone know for sure?  I need to shop around & consider the best car to purchase...  Here to ship or there to buy? 
2.  a) Where else can I go to get the vehicle I'm looking for; Location or Website?  Any good Flea Markets? 
          [ Pulgero - No Auctions (Subastas) ]? 
      b) What are the steps to take (before & after) once the sale is done (pending seller purchased from)? 
3.  Finally, As I had previously mentioned,
      I will be staying in Puerto Rico, several months at a time (for the next few years) until I am there to stay in 2019. 
Registering each year could be a problem.  I'd probably return (to PR) days, weeks or months after registration has expired, What concerns should I have if I did this late, continuously?  Not even sure of penalties or if there are any loop holes given the circumstance?  (I'd rather not give the keys to someone but I may not have a choice.)

All or any advice provided will be greatly appreciated...