Re: John/Lucy BENNETT
Your statement that the dates in the writing are not accurate may be incorrect. The party of over 100 may have well left out of Virginia in 1799. This does not mean that John Hawkins had not first made a settlement in KY in an earlier year. It was quite common for one to come first, make the settlement and then go back and bring the family, and as was quite common, other families to the new settlement.
The surnames written as having been given in the speech can most certainly be proved to have moved from one place to another together, and to have married to one another.