Planing to replace 20 year old roof on Single Family home size 1800 sqft. 

Only with the plane you have 3 days of transition training so you dont kill yourself LOL 

As @Barry Pekin stated above, you're behind the proverbial 8-ball by jumping out of the plane and then trying to figure out how to operate the parachute.

I read a lot and here is what I understand that would work best... if anyone has a better/quicker way, or if what I'm planing doesn't make sense, please advice me... 1.

I read a lot and here is what I understand that would work best... if anyone has a better/quicker way, or if what I'm planing doesn't make sense, please advice me... 1.

In our market we routinely see plane loads of tourists from China and Japan in the summer months.

Demand, location, positive cash flow whether you are financing it or not, area growth, amenities, repairs, seller motivation, is it in a flood plane  economical pluses or minuses, property age, layout, historical issues, future projections, neighborhood issues, weather issues that are negative or positive, distance from an existing public protection, if provided, storage area, and property taxes. 

I’m just planing out some contingencies.

I'm in Canada and find it faster and cheaper to fly, so I put the plane ticket on my taxes (normal economy ticket).  

No way in hell we are cancelling unless a plane refuses to take off or airports shut down.