I was not able to find out much about the Gaskin(s) side of the family. However, My gr-grandparents did have a first son by the name of James A Wynn. He died young from pneumonia (was told he got caught in a bad rain storm) and was lame from an horse & buggy accident. If you search the 1885 Florida census, you can find the Gaskins & Winn/Wynn families living next door to each other in Hamilton County FL. Here is what I have from this post: 1885 Fl state census:
Hamilton County FL
William & Nancy Gaskins are farming.
Ellafair is gone from the household (believed she married into the Mooring)
M Gaskins is 18 and at home. (this is Mahala, my gr-grandmother)
Willy Winn is 20 and listed as a servant. (my gr-grandfather)
There is a WINN family right next door but John is 38 and could not be Willy's father. This puts a new twist on Willy's parentage

I hope this helps I know how frustrating genealogy can be. For further help, you can reference the Popell or Popwell lines as Nancy Gaskins was the daughter of Paul A Poppell of Madison County FL.