More markers to separate them

I have certainly found, and been given, a great deal of information which will help me separate all of the Johns, Georges etc..
This indenture naming James Owens Jr. is helpful because it identifies the James referred to as Junior as being married to Fanny. The other James married to Sally Broshears must be the James referred to as Senior? So now I know that my James D. Owens didn't own the property near the Broshears on Turtle. That was James Owens Sr..

From Karen Degroote

A great source of information about the John Owens 2 and Susannah family are the probate/orphans court records. We get the names of all the children which helps to identify the family group when they relocate from Pennsylvania to Kentucky. The ages are helpful to although, unfortunately, ages aren't provided for individual children. We can come up with a general age range

Since David made his own choice of guardians we know he is over 14 yrs. of age which was the age when you could select your own guardian.

Same for John Owens 3:

The minor children of John Owens 2

This probate document gives date ranges for children without names:

Age ranges presented in probate papers April 3, 1781:

1. One under 5 months. "He being under 5 months old." Do they mean boy?
2. Twins 2 years 5 months
3. One child 4 years 6 months

So we have a couple of children born before 1776 and 4 between  1776 and 1781.

Matching the children with the ages is the challenging part. Although the order in which the children are named in the probate may be a hint to the birth order?