Methinks from the level of your questions, your man with enough money to buy or lease a Boeing should not begrudge employing a proper consultant.
Good ones charge about $800 to $900 USD a day, plus travel and hotels have to be at a reasonable standard. Cowboys come cheaper.
It could be a 10,000 dollar job or a 50,000 dollar job depending on what you already have in place. Overall start up costs will be many times more than that. But get it wrong and the losses will run into hundreds of thousands, if not millions.
As for pilot salaries, this varies with supply and demand and local cost of living, but in your part of the world I am guessing pretty cheap. Maybe $200,000 to 250,000 a year per crew? Because you have to figure in all sorts of add-on costs above the basic pay, like allowances, simulator etc.
If your man's eyes water at those sums of money, aviation is not for him.
PM me only if you are serious, and I will be happy to give you a name.