223 years in the making!!! I finally found my 4x Great grandfather John Young!!! I could just kick myself because it was staring me in the face all this time and I overlooked him. A transcription error on the census record in ancestry.com made it look like he was born in 1840 instead of 1790.
Lesson #1: It always pays to look at the ACTUAL record (and use that magnifying feature) and not rely on the search results.
Lesson #2: Look at the neighbors. I checked the census records from 1860-1880 (my ancestors were free in 1860) and also recorded who were their neighbors. I cross referenced against the SC Archives and actually found a will with my 5x great grandmother's name Flora in it. This will provided boundaries, named the neighbors and provided marriage info.
It was literally walking down the street 200 years ago.
Lesson #3: Track the professions. Not everyone was a farmer. My 4x Great Grandfather was a skilled Carpenter. I havent been able to figure out how my family was free prior to 1860. Did he purchase his families' freedom or did his children marry free persons of color? I did locate who the white Young was (with the help of <a>Victori</a>) that were the slaveowners but I still havent found any wills or manumissions.
Lesson #4: Geography. Its best to know when the county was formed and the outlying districts. I guess I am going to have to pay a personal visit to Barnwell, SC and get actual documents from the town hall.