With just 1000hrs in a C208, all of it over inhospitable bush I'd have no hesitation in supporting this.
There must be a huge untapped market out there for this sort of thing as long as it isn't strangled by the bureaucrats, not to mention an excellent training ground for newbies and a big stir-up of the employment scene.
It us done safely and routinely all over the world, why not here?
But how many pilots? One or two? I expect a second "pilot" who is in reality no more than an employed passenger would knock the bottom line out of the balance sheet and cripple the whole thing. Else second pilots will be paid nowt which isn't progress. Even so that's a waste of 80Kg of payload.
FO Kite, that's the system FedEx have been using for decades. They operate hundreds of Caravans - see their website.