If I get fired after one flight, too bad soo sad, I better have a contract proving that this one flight was conducted under "Private carriage".
That is OK but the pilot has to be very careful to not pay for anything himself; the "wealthy individual" has to be the one signing all the contracts and making all the payments.
Pilots don't want to pay because they are frugal not because it's illegal.
Besides the amounts we are talking about are usually waaaaaay beyond the budget of a pilot.
I've never seen a corporate pilot advancing a $5000 fuel bill for the boss man.
Or $2000 catering including the bubbly.
And how does that work with freelance ferry pilots?
[(a) This subpart prescribes operating rules, in addition to those prescribed in other subparts of this part, governing the operation of large airplanes of U.S. registry, turbojet-powered multiengine civil airplanes of U.S. registry, and fractional ownership program aircraft of U.S. registry that are operating under subpart K of this part in operations not involving common carriage. The operating rules in this subpart do not apply to those aircraft when they are required to be operated under parts 121, 125, 129, 135, and 137 of this chapter. (Section 91.409 prescribes an inspection program for large and for turbine-powered (turbojet and turboprop) multiengine airplanes and turbine-powered rotorcraft of U.S. registry when they are operated under this part or part 129 or 137.)
(b) Operations that may be conducted under the rules in this subpart instead of those in parts 121, 129, 135, and 137 of this chapter when common carriage is not involved, include--]
(1) Ferry or training flights;
(2) Aerial work operations such as aerial photography or survey, or pipeline patrol, but not including fire fighting operations;
(3) Flights for the demonstration of an airplane to prospective customers when no charge is made except for those specified in paragraph (d) of this section;
(4) Flights conducted by the operator of an airplane for his personal transportation, or the transportation of his guests when no charge, assessment, or fee is made for the transportation;
FAR Part 91 Sec. 91.501 effective as of 11/17/2003