Hi @kira golden what parts of the island have you been investing in?

Before price reduction seriously consider kitchen island with seating (2 seats, maybe 3 would fit?).

GO TO REDFIN,  SEARCH YOUR FAVORITE ZIP CODELOOK UP WHATEVER PROPERTY TYPE YOU WANT AND GO TO "SOLD" PROPERTIES WITHIN THE PAST 3 MONTHS ONLY OR EARLIER GO DOWN THE PAGE AND CLICK "DOWNLOAD ALL"IT WILL THEN PROMPT YOU TO OPEN AN EXCEL DOC- OPEN IT-FROM THERE FILTER THE PROPERTY PRICE LARGEST TO SMALLESTFIND THE AVERAGE PRICE BY HIGHLIGHTING THE ENTIRE "LIST PRICE" COLUMN OF THE SOLD PROPERTY SPREADSHEETAFTER CLICKING THE "AVERAGE" FUNCTION, YOU WILL BE GIVEN A DOLLAR AMOUNT- (BOLD THAT FIGURE) THEN GO TO THE SQUARE FEET COLUMN  AND DO THE SAME- FIND THE AVERAGE SQUARE FOOTAGE - THEN CLICK "AVERAGE" HIGHLIGHT THAT FIGURE TOODIVIDE THE AVERAGE DOLLAR AMOUNT OF ALL THE PROPERTIES SOLD WITHIN MAX 3 MONTHS FROM THE AVERAGE FIGURED SQUARE FOOTAGE TO GET YOUR MEDIAN PRICE PER SQUARE FOOTYOU WILL USE THIS FIGURE TO DETERMINE IF A PROPERTY WITHIN YOUR PREFERRED AREA CODE IS DEEPLY DISCOUNTEDTHEN, YOU WILL GO BACK TO REDFIN AND CHANGE THE SOLD TO ACTIVE AND DO ALL THE FILTERS PER YOUR PREFERENCE- "PUT IN KEYWORD AREA- "TLC" "CASH PURCHASE" , "NO FHA" AND "UNINSURED" AS WELL AS HAD A PRICE REDUCTION - EITHER MUTLTIPLE OR AT SOME POINT WHILE IT WAS LISTED HAS A REDUCTION (THIS USUALLY MEANS SELLER HAD HIS LISTING AGENT REDUCE PRICE BECAUSE HE WANTS TO SELL QUICKLY- ) SO IF A PROPERTY YOU FIND (AND THERE ARE A LOT) HAVE HAD 3 REDUCTIONS IN PRICE AND HAS BEEN LISTED FOR AWHILE...

Key west offers the highest of $1,786,950.00 and Naples-Marco Island slightly above $1.4M. 

I live in the San Juan area and agree there are a ton of abandoned properties all over the island. 

You either need to become an expert and do SEO yourself or hire an agency that has a complete plan and roadmap for getting you to a place where organic motivated leads are flowing to your site at a rate where you are taking down profitable deals each monthMike Plactere of We Buy Long Island Homes Fast is a perfect case study of someone who used this approach and is dominating his market.  

First off last year at our annual tax sale the largest overage that year was $40,000 over the tax due.

To illustrate the other side, the rest of the island (outside of these resort zones) has historically been a place where owners can only do MTR's - 30 day + stays, but new legislation just got passed and it's looking like a minimum 90 day stay will be required.

They are one of the largest residential REIAs in the county.

Our largest issue (and I understand how fortunate we are so not complaining...too much), is the enormous amount of taxes we pay.