The problem Flytenow and its pilots ran into is that the FAA decided that participants were operating as common carriers, and flying for a common carrier requires a commercial license.
The FAA defines common carriage as a service meeting four elements: (1) a holding out of a willingness to (2) transport persons or property (3) from place to place (4) for compensation. Elements #1 and #4 are the key elements.
Flytenow argued that its service does not meet either of those. They lost on #4 because expense sharing is compensation. It doesn't matter that it is a form of compensation that is allowed for non-commercial pilots. They lost on #1, I think based on skimming the court's opinion [1], because their service is easily available to the general public.
Note that the FAA does not have a problem with non-commercial pilots sharing expenses with passengers when they are not doing it in a way so readily available to the general public. 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. Even putting a notice on the bulletin board at work, where it might be seen by dozens of people, that you are taking that trip and asking if anyone wants to come along and share expenses would almost certainly be fine.
[1] https://www.cadc.uscourts.gov/internet/opinions.nsf/77E3D4B7...
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...
"A private pilot may not pay less than the pro rata share of the operating expenses of a flight with passengers, provided the expenses involve only fuel, oil, airport expenditures, or rental fees."
But anyway, I completely agree with you, any private pilot who took part in this service is asking for their certificate to be suspended. This is definitely outside the scope of that exception and is asking for problems by allowing private pilots to take part.
Edit: Just noticed that their FAQ still claim that this is completely okay for a private pilot to use [2]. This should be removed.
[1] http://www.ecfr.gov/cgi-bin/text-idx?SID=69df887b632147859ca...
According to the Wikipedia link you posted, a "$100 hamburger" is an excuse a pilot will make for the opportunity to fly. It has nothing to do with covertly charging for a private flight.
You are, however, allowed to split expenses evenly with passengers -- provided everyone is sharing the same common purpose (e.g. flying for fun). But the key part here is that the pilot isn't allowed to receive anything that could be remotely interpreted as compensation.
Right, I know. I was trying to introduce the concept to a group of people who had probably never heard of it - while also showing that it's a real thing that a group of pilots get together just to fly somewhere.
If the restriction is to keep pilots or planes who are not flight worthy from being in the air then take a more direct approach. If the idea is to keep people from competing with private charters and the like then come out and say so.
While I'm skeptical of many of the effectiveness and true purpose behind many measures that are supposed to ensure safety, this restriction is not senseless or absurd.
One of such restrictions is that unless you have a Commercial license, you can't take compensation for the flight[1]. Even so far as to have a passenger pay for a "$100 hamburger." [2]
[1]FAR 61.113(a) states that "no person who holds a private pilot certificate may act as pilot in command of an aircraft that is carrying passengers or property for compensation or hire; nor may that person, for compensation or hire, act as pilot in command of an aircraft." The legal definition of "compensation" is broader than just meaning that money was exchanged. If the pilot gains any economic advantage, it could be considered compensation--for example, the acquisition (and thus building) of flight time, or the fostering of business goodwill, and excessive reimbursement of flight expenses, including payment for meals or lodging.
[2]https://en.wikipedia.org/wiki/$100_hamburger