I've tried, without success, to find the surname Ratleff or some variant in RI, MA, ME etc, but have not found many - and no Eunice/Agnes. Maybe someone else has found some clue as to who she was but I've come up empty.
James, Bruce Douglass also descends from Elisha and he's the one who did the y-DNA test. If you check the Douglas DNA (FTDNA) results page you'll find a listing "from an ancestor of William Douglass 1610, New London" and among those listed is John b 1695. I'm not sure how the Ancestry results match up with FTDNA results, but I'm interested if they correlate at all. Bruce matches my Douglass cousin within just one step on 2 markers. And one of the markers is a slow mutating one that appears to be almost unique to our particular line.
One descendant of John of Middleborough has done a y-DNA test and it appears there is a fairly close link to the line of William Douglas b 1609/10 "of New London" but the link may be back in the UK. The haplogroup is R-269. I've found no records of John's actual arrival in America nor to whom he was indentured or who he worked for as a young boy when he arrived. I can tell you he m Eunice/Agnes Ratleff in Jamestown RI abt March1716/7 and their first child, John, was b in Jamestown Jan 4 1717/18. Joshua Lufkin Douglass' book on John Douglass and his descendants misses several children of John and Agnes.
The more information you can give about the people you mention, the more chance there is of someone else connecting with your family.
Dates and places of births, deaths and marriages all help to place families.
Professions also help.
'My great-grandmother mother was a Douglas from Montrose' does not give many clues to follow up! But a bit of flesh on the bones makes further research possible. But if we are told who she married, what his profession was and where the children were baptised, then we can get to work.
Maybe it is time to update the information in your profile?