I read your post and realized that it represented what I did for a long time.
Having owned and run an operation from scratch for 20+ years involving light singles to medium twins in a tropical island environment, I would have to say that your first point of reference might be someone who has actually done it.
That means visiting with or consulting (preferably through contacts) people who have either owned such an operation and therefore experienced the numerous challenges, or someone who has intimate knowledge of running such an operation. It certainly requires a lot of planning and thought.
A consulting 'pro' might have notions but unless they've actually been involved over a period of time (paying the bills, negotiating with multi jurisdictional/regulatory/planning/customs/people, managing logistical support, identifying personnel that will actually fit your organization, selecting aircraft that will be most suited to the type of operation/environment/people available, considering other operational/competitive challenges) etc then they might not be able to be objective/practical for your long term successs. Even then operational financial success (it may even be considered a cost of doing business in support of hotel operations) for any operator in this industry is not assured by any stretch.
Without knowing a lot more detail, I could not even begin to offer anything but the most cursory thoughts. I would urge you to consider some of the things that I mentioned above sooner rather than later, more than just what aircraft to buy.