Understanding the preferences of the Hamptons luxury market is essential.

But if I had a lot more liquid capital and had the choice, I would buy newer ones.

@Edgar Duarte Depends on if you prefer owning real estate or want to be invested in the stock market.

This gave us peace of mind and ensured that any unexpected incidents wouldn't result in major financial setbacks.These two choices have played a crucial role in optimizing our STR strategy, balancing profitability and protection.

IF you plan on going back someday, and this is the home you want to move back to, then renting it would be a good idea as long as you estimate that it will cover itself, or preferably, cash flow, which it appears that yours will at @ $2K or so per month (after expenses). 

I went with the conventional option for a few reasons, but that's not the best choice for everyone.

My number 1 tip would be to go off market and find owner that wants to sell at a discount / prefers speed and convenience. 

Preferably stay for one year and find another house.

As for serviceability, I personally prefer kohler as a plumber.

He had no choice but to begin selling off the portfolio.