The only reason I like it is that I live here and have systems to buy deals under market value.  

Starting out, buy a shabby condo and live-in/flip it.

I'm quite not 100% on wether or not if I purchase my first investment property where I currently live (Virginia) (*which I will be*). should I also gain my license here since I'll have a property within Virginia.

The port of Puntarenas is lively.

Most bankers can run live pricing to help you make a final decision without having to have your credit pulled several times or fill out a dozen applications and submit docs!

Convince yourself that there's a better than average chance that you will lose, and if you can live with the time, energy and money spent if you do. 

Fannie Mae has a requirement that if you want to use the rental income from the non occupied units, that you MUST have a current housing expense which means you cannot live rent free.

They can't assess all the subjective data like overall layout, view from the living room window, the dogs next door that bark all day, the width of doorways, size of individual rooms, quality of kitchen cabinets and appliances, etc.The best thing to do is study your market regularly.

But, I'm fairly risk averse, and do live in a heavily tenant leaning area as far as regulations and court judgements. 

If you are doing a live-in flip why not use that equity for a down payment with a refi or HELOC?