The origins for Pleasure Island came from places just like the Baltimore waterfront project. Disney wanted an adult/nighttime entertainment district and they used the "refurbished harbor" model as the theme complete with the overly elaborate backstory of Meriwether Pleasure and his sail making factory.
The outsourcing of Pleasure Island is the result of the current business model at WDW. Disney continues to require significant profit growth from, yet the overall business itself has hit a plateau. As is demonstrated with Animal Kingdom, the resort simply can't continue to increase the number of people coming to the resort.
One way is to make more money from existing facilities. Current thinking is that Disney will make more money if it simply collects rent rather than run facilities. Let someone else worry about staffing and utilities and profit margins and pleasing the guests.
If it's handled well, this can actually be a good thing for the park. For decades
Disneyland leased out shops and restaurants to outside companies. They offered a unique and much broader range of products and services than Disney could offer on its own: from Pendleton woolen goods to pianos and antiques to one-of-a-kind flavors of Carnation ice cream (and WDW's Dole Whips have nothing on the old Welch's Concord Grape Slushes from the old Fantasyland). This practice was also used when World Showcase opened so that the restaurants would be operated by companies from the countries they represent.
Of course, it can also be a bad thing. A huge problem with Disneyland's Downtown is that every store there can be found at least one other mall within a twenty minute drive. The development has become a bland and generic experience with low sales and constant turnover. Without anything unique, there is no reason for locals to go (and there aren't enough retail tourists to support it).
Perhaps we'll get lucky and someone enterprising business person will come up with a facility as unique and interesting as the Adventurer's Club. Sadly I think Disney's going to set the rents and the guarantees so high all we'll get is another chain restaurant. And WDW will become just a little less interesting.
if I recall correctly. 
