It's a winning combination of direct access to industry experts coupled with building lasting relationships and get direct feedback on your strategies in small-group format.

-Management is low - you'll need at least 10% plus leasing costs - typically a month's rent for each lease-up, and sometimes a renewal fee as well-Insurance seems low-Are taxes accurate? 

Friendship and business don’t always mix well, so it’s critical to use a solid lease and treat this as a business arrangement.

Companies know where they will be treated well and where they are not wanted.

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

So if you are using that site or something similar you could very well over pay for the home.

Locations that are a 0-1 hour car ride from san juan to a nice town/city with more affordable areas walking distance to the beach would be interesting as well. 

@Samuel Coronado - the challenge is that there will likely be a very small number of renters looking for a house that size, as well as that can afford a rent amount that high who won't just buy otherwise. 

(Could be more than just two) So just be aware, you can use the sec 8 income to help with qualifying for a DSCR loan but you could very well end up with a higher rate.  

We've utilized the VA loan for our current home, and this strategy has worked well so far.