That's all you can do given your experience. $80k in equity isn't much in the grand scheme of things.

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? 

I manage around 400 rentals with 14 years of experience and have never been sued once.

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.

What is your experience with Obie insuarnce and Safeside insurance ?

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

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

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".