Self chauffeuring is about as dangerous as being one'w own legal counsel in a criminal proceeding.
My advice is to have him decide whether he wants to be Helicopter Pilot or Businessman.....and if he wishes to keep his finger in the business...just do the helicopter flying as a hobby.
The risk of business decisions over-riding flying decisions is just too great for most folks to cope with. It is a very rare individual that can compartmentalize to the degree needed when the weather turns bad, a maintenance issue arises, or one just must be there at a certain time and place.
Otherwise....do his training....get the license....find the helicopter and buy what he wants. If he wants the Jet Ranger....take his lessons in one...do the license in one....and then buy one.
No sense exposing himself to a Robbie needlessly.