Great question! The profile has the sticker coded to add the Kentucky Appalachians category, saying he lived in Kentucky, which might not be best considering that's where they died while moving from North Carolina to Kentucky (I'd recommend changing state=Kentucky to state=North Carolina & adding app-cat1=North Carolina).
If he were born in Virginia, it's likely he was born in Augusta County (where his parents were from), which at that time extended west into Appalachia, so you could add three of the project's categories for people profiles: Virginia Appalachians, Kentucky Appalachians, and North Carolina Appalachians. However, looking at the locations in the datafields for his parents & siblings, the family might have been in North Carolina already at the time of his birth (so scratch the Virginia Appalachians category for him).
The appropriate location categories, as evidenced by other comments, are a bit more complicated. Considering the datafield entries for where he married and where his children were born, coupled with those for his siblings, it would seem that he lived most of his life in North Carolina - Rowan and Burke Counties as a married man (Burke County today is in Appalachia & it is likely that the areas the family lived in were in Appalachia then).
So... location categories:
There is not a category for Cumberland Gap, but there is for Wilderness Road (Wikipedia says the Cumberland Gap "was an important part of the Wilderness Road").