Love the story and how I can literally feel you beaming from a couple thousand miles away!!!!! 
He has the temperament for it for sure- someone who is "no drama". 
A couple years ago, there was a then 18 year old over here on the east coast who flew banner planes at the shore (story reported on our local Philly stations since we cover the south Jersey media market) who was forced to land his plane on a causeway near Ocean City, NJ. He was from Wyoming and had gotten the job at the Jersey shore to build up flight hours. Calm, cool, collected.
I ended up delving into that company the kid worked for and had seen a few videos of how those planes actually took off with a hook on the rear, would swoop down to fly low over the banner mount point, snag it, and then ascend again, heading to the destination.
Found a similar video of that, which was pretty cool (along with the history of that technique) -
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