As I’ve just had a very bad experience with a contractor, is there a contractor contract template that someone would be willing to share? 

She updates my books twice a month.Try to find one who has real estate experience.

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.

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 ?

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? 

Your rental agreement with a detailer is going to depend on the experience, quality and track record of the detailer.  

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