What is the cost of zoning 150+ acres and obtaining the needed permits to build the golf course? Maybe $25,000 to $1MM+ in places like CA? Does the land owner/speculator come-out of pocket to fund these costs? I doubt that there is traditional financing for this approach as in this case, the "improvements" (the "entitlement"), produce no additional cash flow and its collateral value is speculative at best.
While zoning may be permanent until an owner applies for a change, I believe that permits in most places have a limited shelf life. Perhaps a specif use plan development sans the permits could be obtained, but if the land owner had the wherewithall to divine what the market needs X years out, he would likely develop the property himself.
As was also pointed out earlier, EPA, flood, and wetlands regulations change all the time. As far as I know, today's regulations/limits cannot be grandfathered until the property is developed X years from now (states can normally impose more stringent requirements than the feds, but not less).
In the Bandon example, Keiser got a relative bargain because he assumed the risk that the property could be developed to a higher use than the present zoning allowed. He rolled the dice and won. In theory, if the original land owner had access to the $$$$ to secure the entitlement, he could have taken the risk himself years earlier, and someone like Keiser may have paid a premium. Or perhaps not, and the current owner would have spent all the time, money, and effort for naught. In the worst case, if he got a lender involved and mortgaged the land, he could have lost it.
Another thing to consider is whether the original owner can maintain his agricultural exemption after receiving the entitlement. In many areas, the pulling of permits triggers the change in the tax classification of the property, and taxes can go up astronomically over night (plus roll-backs for up to five years in some states).
About the only scenario where I see considerable benefit in something like an entitlement is when an owner can do things with the property that the buyer and developer may not be able to do otherwise. For example, I believe that a farmer or a rancher might be able to do more with wetlands on his property than a golf developer. Or a prominent member of the community, say a mayor, can be involved with a group of local owners and shepherd through zoning and variances that an outsider would not be able to obtain. The property is then sold with the approvals in place at a premium. Under this scenario, however, the term to development is usually months, not years.
I still would like to know the states where this entitlement thing is prevelant. Perhaps I am missing something which may be usefull for a potential client, and I am willing to research it.