Time is your biggest ally in deals like this. 

A lot has already been said, but having been both an owner who used third-party managers and now managing properties for others the biggest thing is setting up expectations and responsibilities clearly.Also, if you don't understand something don't hesitate or be afraid to ask!

My biggest problem is with Booking.com.

I'm not sure about you but a broke government is almost always a deal breaker for me when it comes to investing in real estate.Finally, while Puerto Rico has had its fair share of devastation from hurricanes and Haiti from earthquakes, the Dominican Republic has been mostly escaping from both (yet all good construction there is hurricane- and earthquake-resistant).

The biggest is they have the entire property, not just a room and it feels like home.

Morris pulled out many of the tactics of those days.the biggest was his take away close technique.. your interested.. well we are so busy that we cant talk to you for 3 months and 5 days and you getter be at your appointment when its your time.. then get them on the phone and  they like a certain  property and they reply  sorry that sold.. now you have this false sense of urgency and they just jump at the next one.

The dog and bed bugs are my biggest concern.

The biggest down to this deal for me is the "partial" disruption of my SF BRRRR model that is currently making my 120k yr income. 

The biggest hurdle self-managers face right now is changing laws.

But you may be more comfortable with earthquakes, or tornados than hurricanes.