Just realized now that I haven't posted anything since the end of July so I figured I'd best do something about that. I'm still digging, though I haven't found anything of any great significance in a little while. Still reading everything I can get my hands on that even mention a Gray in eastern and southern states and in Nova Scotia. Mainly I've been doing a lot of filling in names and dates of distant relatives, like 3rd cousins twice removed and stuff like that. I still keep finding a lot of repetition in names that are familiar throughout the parts I already do know about ... so it's good to be reassured even when I'm off on a distant trail that I'm still on the right track.
I've seen some intermingling with families named Crocker, Cann, Robbins, and more. In the case of Capt Jesse vs Mary Postell there was a similar dispute between a Joseph Robbins and two of his slaves. Robbins had also been in St Augustine at the same time as Capt Jesse, he moved to Nova Scotia around the same time, and also lived in Kemptville. They were both friends with the Andrews, Fannings, and Mangums, and had several dealings with each other, and there are some Robbins in my tree (haha!) that lead back to Joseph.
It's so weird finding out that I'm related to these names that I've heard my entire life and had no idea. Of course, they didn't either, it's all pretty much lost history.
Anyhow, back to the digging I go ... hopefully I'll match up some more names that will lead somewhere other than down the rabbit hole again.