I am curious if there is anyone with experience in owning real estate in another country being a US working citizen and have some tips on how taxes operate if I were to list that property on Airbnb in a foreign country and so on (any other tips you can offer towards this)...

Ask how many units they manage and how much experience they have.

Anyone has experience doing mid-term rental in this SA for travel nurses?

It's the land/location increasing in value - not the home itself, in my personal experience and opinion

What is your experience with Obie insuarnce and Safeside insurance ?

Property is affordable and looks good on paper, but your actual experience may be very different due to costly turnovers, bad renters, vacancies, etc. 

Yeah at the time I was a foreman on a construction crew for a local contractor/my beat friend and mentor, so I had a truck full of all the tools, access to leftover materiels needed as well as a significant amount of experience so yes I personally added a second bathroom and as far as the 5th bedroom goes, it was just a matter of putting a door on the "living room".

What has been the experience of the "Millennial" and those coming there after? 

My experience has taught me that it is just a human nature to seek the most benefit for them at any cost, even if it means harming someone who facilitates profitable transaction serving their interests.

With my limited experience explained, here's the situation.I have ear marked a good amount to start real estate investing.