Oh boy. Lots of misinformation here.
Don't get too wrapped up in the idea that holding out is the only criteria to determine if a flight should be conducted under Part 135.
In the first scenario, the owner of an aircraft has hired a pilot to fly that aircraft. Nothing wrong with that. But is it a Part 91 operation? Well that really depends on the circumstances, doesn't it? (it does). In scenario #1, the question is asked if the pilot may be compensated for his or her services. The answer is simple; yes, so long as he or she holds a commercial pilot certificate.
I the first scenario, if the owner elects to carry passengers (fiends, family, business associates, pets, little green men from mars, or the M&M guys), that's just fine. When it doesn't become fine is when the owner seeks reimbursement or money for taking those passengers. If the owner is going to the Bahamas and invites Cousin Mabel, CEO Bergman, and Alice Krauseman's cat, that's okay. If the cat pays, it's not okay.
Moving to scenario #2, the question is asked:
Now, let's say, your friends ask your pilot to take your Lear and fly them to a business meeting in another state for a fee. Does it then become Part 135?
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The answer is Yes. It is covered under Part 135. Does the flight land at a point other than the point of origin, and is it carrying persons or property for compensation or hire? Why, yes, it is. Is that flight then required to be operated under Part 135? Why yes, it is.
Has the flight been held out? Probably. If the friends who wanted to fly knew enough to ask about transit to the destination, then the flight was held out. Holding out doesn't need to be advertising. It can be word of mouth, reputation, or any other method by which a passenger learns of the availability of transportation. However, demonstrating weather or not the crew or owner held out isn't necessary to show that the flight must have been conducted under Part 135. The mere fact that a fee is paid and that passengers or property have been conveyed to another location other than the point of departure, is sufficient. Additionally, there is no common purpose between the use of the aircraft by the pilots, and the paying passengers going to the meeting.
In scenario 2 to be Part 91 it would mean no holding out and only shared prorata expense with the owner who has a shared purpose for the trip (no compensation for trip other than half the expenses)
Again, no. Don't confuse the issue of cost sharing by a private pilot,with this scenario. Going dutch (pro rata) doesn't excuse the operation. The pilot is not the owner; it is a paid pilot. This is not a scenario where a private pilot is trying to share costs with a passenger. Weather the passengers share in the cost with the owner or not isn't relevant. The owner isn't the pilot. If the passengers pay a fee at all, then it's going to be a Part 135 operation (or violation thereof).
Now you are getting into a gray area. I think this goes back to the whole private pilot idea of "sharing expenses".
No, really it doesn't.
If you did not hold out or exhibit a willingness to carry for the general public, then you can carry passengers or propety for compensation under 91.
Oh really?
On the other hand, if you were a corporate operator, and you owned a business, and you wanted to fly an important client in from Chicago to sell him on a million units of your new "widget", you would fly him in for free, and it would be considered a business expense. Your revenue woud come from the sale of "widgets", not from the operation of the aircraft.
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The sale of widgets is incidental to the flight. However, if the sale was contingent on getting the "free flight", it's no longer incidental, is an economic benifit derived as compensation for the flight, and is illegal. Additionally, if the owner does receive reimbursement from that important client for the flight from Chicago, it's a Part 135 flight.
gotcha, so under 91 and private carriage(when no holding out is involved), an operating certificate is not needed
Not true. The circumstances dictate. Simply suggesting that because holding out did not occur (and ya gotta be careful on that one) that it's not a Par 135 operation, is a risky game. Not so. If the fee gets charged for the transit of the pax or cargo, it's no longer simply a 91 operation.