I'm in the business of real estate, not internet clout, but whatever makes you feel good about yourself buddy!

And I'd bet your 'Contractor' is not licensed or is not very good compared to typical standards...But good luck....

And if your LT tenant needs to assist with things now and then, be sure to show appreciation and compensation of some sort (I've offered free wifi, though my tenant prefers their own internet/cable).3) I haven't had any issues, but maybe avoiding carpet and low rates with single night rentals that ends up attracting homeless guests.

Stewart Title here in SA will be your best bet 

Of course, this is just my opinion but I bet I'm not alone..If I'm an investor, I think the returns you're able to achieve in Costa Rica are higher than normal because you focus on these large properties and, as @Martin D. mentioned, prices in that country are too high and returns too low.

This is not available in smaller cities.You can evaluate all these criteria from anywhere in the world using the internet.

I'd also go in with your own agent.I'd bet the listing agent's company is keeping the deposit even though it is meant to be in trust. 

I am not sure they would be comfortable with me blasting their contact info all over internet. 

Figure out all the extra expenses of utilities, management, perhaps hot tub, internet etc. go low on income and high on expenses and see how the numbers look.

In-unit laundry is a must-have, and high-speed internet is essential for your guests, especially those staying for work purposes.