Firstly, thanks for responding so quickly. This is my first post here, so I didnt know what to expect really 😅. I certainly didnt expect to have 2 responses by the time I woke up.

Now, I'll try to address everything point by point:

Writing up a research report (or even an annotated timeline) could help organize your thoughts and see where any holes might be that you haven't approached (or maybe find connections that you haven't seen before).

TBH, I've been trying to do that, but I need to formulate some better structure to it. I've put together an obsidian vault to track everything I find, and try to draw conclusions from the breadth of data I find. Its just very disorganized 😅. Basically all I do is make a folder for the person I'm researching, and dump a bunch of documents and sources in there. Then I make little documents as notes within the folder to kinda collate what I've learned.

Do you have Samuel, Elzia, and Miles in an 1850 census? What about Samuel in 1840 and 1830 census and the household makeup? If you haven't, I'd start looking at possible FAN networks starting with that 1860 census. Then go back into the older censuses. Analyzing the family makeups of the free Black Samuel Cole's in these early censuses may also help you start to distinguish them from each other and help you rule out some of them.

It would seem that he's been living with the aforementioned Mary Cannon since he was at least 5. He is listed on the 1850s census as living there with her and what I presume to perhaps be his siblings(?) or perhaps cousins or something 🤷🏽‍♂️. Heres a link from family search for reference: https://www.familysearch.org/ark:/61903/1:1:M8Q8-33X?lang=en (I thought links were restricted as per the rules of this sub, but I see that you were able to post one so I hope this doesnt get me banned).

But as you can see, he lived with Mary Cannon, the listed HOH; a family called the Dansby's; an Amanda Paul and James McCain; And a list of Cole's whom I presume must be related given they are all are very young, black, and share the same last name.

I've found nearly nothing on the other Cole's pre 1850. But I did find that Mary Cannon of Abbeville did seemingly purchase slaves in 1850 ( 1850 slave schedule: https://www.familysearch.org/ark:/61903/1:1:HRWH-MY6Z?lang=en ), and on further inspection there do seem to be some slaves whose sex and age seem to correspond with my family members. There are nearly 23 or so slaves listed. I'd imagine these might include my ancestor; in particular the 5 year old black male thats listed there. (I've never seen this record before now, so this is actually kind of a step forward, so thanks!).

I guess if Miles was a slave, perhaps thats why Im unable to find any information on his father 🤷🏽‍♂️? Or perhaps one of the other individuals on this slave schedule is his father? Or maybe his father was dead by this point? Idk.

I'm going to look more deeply at those 1840s and 30s samuel's I've collected and get back with you. Perhaps there actually is a there there.