I will look into the Harpswell records for Patch and Witham/Whiteham families.
The Black family of Harpswell is part of the history of Harpswell. It is written that William (Black Will's son) and his son William (the grandson of Black Will) were the first settlers of Bailey Island. The story goes they were forced off the Island by Timothy Bailey and his wife. The Baileys had purchased the land from the Pejepscot Proprietors.
The Black family crossed over onto Orrs Island (where they still live today). The water they crossed over is (to this day) called Will's Gut/Strait. In fact when we named roads for 911, the road closest to that water was named Wills Strait (Rd). William (both the 3rd and 4th) purchased a great deal of property here, which helps in tracking them.
You are providing me much more help than you may realize and we might actually solve the main missing link!!! I would love anyone to jump in with additional info.
On an interesting note. Of the Blacks that live here, Edmund (Rip) Black, Bailey Island is listed as #4 in the 50 greatest sports figures from/of Maine. He won the hammer throw bronze at the 1928 Olympics.