James Obadiah Howard's profile is here
it used to be connected as a son of Edward Francis Howard-1691 and "Mary Chowan", but was disconnected.
His will is given in full on the profile, but I haven't seen a published source.
He mentions a wife Sarah, a daughter Sarah, apparently unmarried, and 5 sons, in no particular order: Solomon (under 20), Edward, John, James, Samuel. Also four brothers: Edward (overseer), Stephen, Joseph, John (overseer). He had bought land in Bertie Precinct NC from the first 3 of those.
James also says he and his wife had a plantation in Nansemond Co VA, so the 5 brothers weren't just a bunch of kids who moved south with their parents. Probably they were all old enough to grab land on arrival.
Looks like James and his brothers were born in VA and all moved south to pick up land in NC. Two of them might have sold up and moved on.
I gather the Nansemond Co records went up in smoke, which is presumably why there's a brick wall here. If he'd patented the plantation there'd be a record in Richmond, but not if he bought it.
The profile of Edward Francis has him dying in Bertie, suggesting that he too is supposed to have trekked south with his alleged sons (possibly all grown up. But the sons now attached to the profile don't include James and his brothers.
My theory is that Edward Francis was originally conjured up by the descendants of the Bertie bunch, and a random assortment of other Howards then hooked themselves on.