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.)