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Re:Uber-Style Flight-Sharing Service Shot Down by U.S. Court by AndrewKemendo on Monday December 21, 2015 @09:42AM (#10771238)
namely expense sharing as long as the pilot is paying his fair share of the flight expenses

That's not compensation. What he is talking about is two pilots, usually broke pilot students at the same FOB, who have their PPL but need hours for their CFI, IFR or some other type rating. So they share gas and then do different legs as pilot in command, it's cheaper, you get your hours and have some company. I can tell you from first hand experience, solo cross-country, is boring as hell. I even did it before GPS was a thing and you have to do IFR landmark based nav - still boring.

If you mention to your coworkers that you are renting a Cessna to fly to some specific place to visit family over the holidays and a co-worker says they want to go there too the FAA would have no problem with you taking them with you and having them pay their share of the expenses.

It's been a while since I flew, but that was definitely one of the things that was drilled into me as "not legal" behavior for a non-commercial pilot. Your scenarios would bust all 4 common carriage rules. "Goodwill (dropping off clients) is not bona fide purpose (likely is compensation)[1]."

[1]https://www.nbaa.org/events/amc/2011/news/presentations/1011...

Re:Uber-Style Flight-Sharing Service Shot Down by U.S. Court by lmm on Monday December 21, 2015 @10:14AM (#10771404)
A coworker is not a client, the point of that restriction is that you can't fly a client to their house for goodwill purposes if you don't have a common purpose for the flight. Sounds like that example would be fine provided the expenses are properly pro-rated and limited to the specified things.
Re:Uber-Style Flight-Sharing Service Shot Down by U.S. Court by tzs on Monday December 21, 2015 @11:48AM (#10771955)
Expense sharing is compensation, although Flytenow tried to argue otherwise. See page 12 of the court's ruling.