Two, has there ever been a discussion of giving the 800 pound gorilla some TEETH by becoming aa incorporated town?

It has, and the consensus has consistently been that the residents of Ocean Pines would never go for it. There's a statute governing the incorporation of a municipality in MD, and it requires, a petition by 25% of the residents, then a favorable vote of the County Commissioners, and then a referendum where 50% of the residents vote for the change.  Anecdotally, it appears that many in the Pines think a becoming a municipality would do more harm than good.  I do not share that view, but I do agree that it would be a tough sell . . .