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.

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!

The port of Puntarenas is lively.

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.

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.

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

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

Quote from @Fernando NA: Hello everyone,I’m considering purchasing a piece of land near Divide, CO, to build a small off-grid log cabin and list it on Airbnb or similar platforms.For those of you who live in the area or have experience with this, I have a few questions:>Is it possible to list such a property on Airbnb given the local regulations?

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. 

I got tired of paying to live in other people’s homes.