I can probably get at least $200 per sq ft on the addition part if I decide to sell -- my house is among the smaller ones in a neighborhood of $1m plus, 4,000 sq ft houses.

Providing more services and amenities for your guests is what's going to continue to help you stand out among the competition and competition is getting fierce so doing more and better than the rest only happens naturally. https://hbkcpa.com/beware-vaca....    

These would be among the questions 

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These repairs are among the most expensive and can easily cost thousands of dollars.

There has been discussion among the legal community that serving a formal notice violates the stay at home order and I suspect tenants and tenants counsel will be using it as a defense to have cases vacated.

Id say St Thomas or St John would be better in terms of location, ease of transportation among the USVI (A few tidbits I observed and noted: The HOAs (fee seems to range 200-500) may not be so bad an idea for a more hands off approach unless, you plan on managing the property yourself; most of the 3/2s I saw were other vacation rentals, not so many in the way of residences for locals; cost of ownership increases much higher in the long run after running the numbers on a few existing rentals due to stamp tax, increasing insurance costs, specifically the hazard insurance (CBS homes have lower premiums); replacement costs for wear and tear due to the salt water…etc.

STR are absolutely in the crosshairs of the politicians and there is growing opposition to them among the people.

Improved durability, improved value, and helps you stand out among the rest.From a reputation standpoint, you'll also earn a reputation for installing higher quality furnishings - never a bad thing.

Here is the link to the extensive report: PWC Emerging Market ReportGuess where Brooklyn ranks among the to 80 Buy and Hold cities?