I did a quick look through the earliest records for James Dennison Scott and I didn't see any purchase of acreage (outside of town) prior to 1820. Most of the transactions have to do with land in Hillsboro:

1809 - Bought land in Hillsboro
1810 - Bought land in Hillsboro from tax collector
1811 - Sold land in Hillsboro
1812 - Sold land in Hillsboro
1814 - Bought land in Hillsboro
etc.

It's possible James acquired his land through a government grant as did many Virginia veterans at the time. Or purchased it before the existing records began.

I check the tax lists but they don't show any early Scotts. According to that book, the earliest book is dated 1826 and after that there are some books missing.

Don