If you wish to consider this as a business proposition (rather than an opportunity to have tax deductible helicopters) then I suggest you consider this from the other end:
How many punters will want to fly the routes you plan?
What is the sort of price they will be prepared to pay?
What other flying than inter-island punter shuttles could you develop?
On that basis, you will be able to get some idea of the revenue you might be able to generate. That would tell you whether the business could afford any helicopter.
As others have said (sadly) what you propose to do does not actually require a helicopter at all. Since other things can do it cheaper, there does not seem to be a business case.