Follow those convo's and you will quickly see who the major players in that space are.Good luck to you.

I saw the details of a beach resort in Barbados .

Real estate is local and if you are trying to invest at a macro level with large sums of money (which he would be doing) it's very difficult to get a durable competitive advantage over a local player that know his/her local market and is mining local deals from motivated sellers.  

On the investment side, however, if you're not plugged in to your local REI group or just getting started like me, it's tough to know who to call to even ask for a quality contractor referral who understands an investor's goals.This is a little less formal, but I recently resorted to working my Facebook network to ask for GC & Subcontractor referrals.

I don't know of any personally, but I imagine that a professional sports player would have made more than enough in a few seasons to get a very good start in REI. 

Once you get the entitlement (conceptual city approval to move forward with designing the development), then all the other team players like the structural engineer (I can help you with that),  MEP consultants, and contractor can joing in with the architect to give you a ballpark/general estimate of what it might cost to design and build the development.

You want to tap into that if you want to be a big player. 

4) Do you have to pay the daily resort fee when you use the unit for personal use? 

Do I have to resort to a hard money loan, or pass on the property?

@Tomas Satas there are many players in the space, but it will depend on the # of units, age and location that determines who if the best fit.