The Legality of Ride Sharing in Aviation

If I want to log two hours of cross-country flight time on a given day, which I will do regardless of having a passenger, is it against regulation to let that ride-sharing passenger pick the destination and split the bill?

What I infer through having read various FAA letters in the past is that there needs to be a personal relationship between the parties (preferably established in-person) in a context outside of "share airplane ride".

Of relevance is the FAA's 1985 Chero letter [1] about a similar Pilot/Passenger sharing: "The PPA system is not a casual one of an individual pilot wishing to take some friends or acquaintances with him on a trip. The PPA system would violate the letter, as well as the spirit, of Section 61.118."

The Haberkorn Letter (2009) [2] has relevant content: "You question whether advertising, on Facebook, the specific time and date of your trip to your "friends/family/acquaintances" would be acceptable as a private pilot, since you do not consider yourself to be holding out to "the general public." As described above, holding out is accomplished when one communicates to the public, or a segment to the public, that transportation services are indiscriminately available to any person with whom contact is made."

In a later paragraph:

"You question whether you may post the specific time and date that you are travelling to Long Island on an FBO's bulletin board in order to carry two additional passengers with in exchange for a pro rata reimbursement of the operating expenses. Again, the FAA cautions that this type of advertising may be construed as holding out (see explanation in question 1 above)."

And in a later paragraph in regards to being reimbursed via PayPal:

"Whether or not such payment comes through an online payment system such as Paypal has no bearing on the legality of this situation. However, payment through Paypal would suggest that there is an interest in carrying passengers with whom there is no previous personal relationship and that the offer to accept passengers is being made to the general public (see concerns raised in question 1 above)."

With regards to how Flytenow describes things: "Flytenow facilitates common purpose because pilots, rather than enthusiasts, unilaterally dictate the destination (and purpose) of an adventure, and enthusiasts express shared interest in the specific date, points of operation, and adventure."

The last time I checked United Airlines unilaterally dictates the destination of their adventures and the specific dates and points of operation. These characteristics do not seem to me to turn the flight into a "bona fide common purpose".

Again, without having explicitly stated it I believe the FAA wants expense-sharing passengers to be: - friends - family - acquaintances

And not just those artificially constructed for the purpose of working around FAA rulings. At least, this is how I'll interpret the FAA rulings & letters until they explicitly state otherwise. Again, IANAL, hope they rule favorably, but wouldn't risk my license to learn the answer is "no".

[1] http://www.beechtalk.com/forums/viewtopic.php?f=7&t=88055&st...

[2]http://www.faa.gov/about/office_org/headquarters_offices/agc...

Flytenow would make this a more attractive proposition by agreeing to pay my attorney fees if the FAA takes action against me because of a Flytenow flight. That would include representing me before the FAA in administrative proceedings and in federal court as far as I choose. (I'm a private pilot, not a commercial pilot.)

Better yet, because I'm not aware of the funding behind Flytenow, put the estimated maximum cost in escrow with a trusted third party such as a bank so it would be available even if Flytenow runs out of money and ceases operation in the middle of the litigation.

Then I'd be more likely to try it, and as an additional benefit the FAA would be less likely to pursue Flytenow-affiliated pilots. (FedGov agencies would rather try to make a test case, all else being equal, of citizens lacking aggressive legal representation.)

To clarify: is the point of the service to offer flight sharing for convenient flights all over New England to get to remote or local airports faster? Or is this only to go flying/sightseeing for fun?

It is not enough to have a commercial rating. If you are engaging in an (technically, almost any) operation which requires a commercial rating, you also need a 2nd class medical certificate and most of those operations would fall into part 135 (charter) or part 121 (scheduled airline service).

The items that a commercial pilot can do under part 91 that a private pilot cannot are very limited in scope: 1. Tow banners 2. Tow gliders 3. Provide sightseeing flights in a 25 mile radius (and landing back at the same airport) 4. Fly certain types of cargo 5. Fly powerline patrol, aerial fishspotting, aerial photography 6. Conduct demo flights for aircraft sales purposes 7. Part of the path towards becoming a paid flight instructor.

None of those are "fly passengers in air taxi operations".

The company seems to be taking the position that they are helping to coordinate already legal Part 91 flights, and it would be inconsistent of them to require a commercial certificate to do that.