Sign in FSDO , Arguing with the FAA is like wrestling with a pig in smud you begin to realize the pig is enjoying it.

Hey Billy Bob can you fly us to the lake next week? Sure but I need you to pay me for plowing your field last week so I can buy gas.

On a more serious note I am on a government regulatory board with five other members. I want to fly our group to a national convention 800 miles away. Is it legal if I do this for no monetary reward? Can I do this legally if I do not smile during the flight demonstrating no compensation by having a good time. If it can be demonstrated that other members of the board laughed or smiled during the flight did I receive compensation? The last night we are on this trip the board decides to buy my dinner, is it legal for me to except as long as I pay my share of the tip? Sounds crazy but that’s what the FAA has come to. I say F em and I want paid for plowing your field.

Everybody's got a cute story they think will work until the enforcement action shows up to change their minds.

Or the tax man:

Back in the day, a local school where I lived was trying to pull the 1099 gag while making the instructors work set hours, wear uniforms, do unpaid desk duty, etc. Basically every item on the 1099/W2 check box.

Those situations persisted longer than you’d think in those pre internet days. But in this case someone dropped the dime to the tax authorities and they can down like a ton of bricks, and lo and behold they found a bunch of other stuff. Hilarity ensued.

It’s never just one thing, either.