He's a flight instructor and we took out his employers 172 for around an hour and a half.The flight should have cost around 150, but his employer comps him an hour for proficiency once a month, so I only paid 58, plus buying our food at 40 ish.

It's important they are articulate and proficient in English so I'm expecting to pay significantly more than someone off-shore.  

It seems like a great Airbnb potential plus a great vacation home for me.I feel confident with overcoming the barrier that I see so far: language (I have minor proficiency and can get a translator), finding a trustworthy local rep to help me (tips would be welcomed on how to do this but my plan would be to use my personal network), navigating local laws (google and lawyers). 

Could one just get proficient with title search and bid with no worries?

--I am a former architect, but then was a stay-at-home mom for the last 20 years (I've done a lot of small jobs on the side for myself and friends, but I only know how to hand-draft; now-a-days you need to be proficient in two or three CAD programs to get a job in an architecture firm!)

Use your education provider's exam prep to determine what areas you're proficient in, and which ones you need a little work.  

I'm not disappointed that they can't provide advice, I've just come to realize that most aren't proficient enough in their departments to be able to do so.  

But I am fully proficient with plumbing/electrical/HVAC/roofing myself, so expenses in the trades do not apply to me except for materials.

If I can't help them do that, I don't deserve to be paid.A lot of people have credentials - doesn't guarantee their proficiency.

If not, may find it hard to get a bank to finance you if you can't demonstrate a proficient history of like-kind construction.