I am familiar with both the English and the Welsh Wynne lines.I think you may have confused the line of Sir John Wynn of Denbighshire, Wales who reside at Wynnstay and are descendants of the original baronet distincted in 1610.These Wynn's are not to be confused with the Wynne's (now Winn's) of Nostell Priory in Yorkshire, England and London who were disticted with a baronetcy in 1660.Both these lines of Wynne claim the same armorial ensigns of Owain Gwynedd but no relationship between them has been yet determined.
Your line of Wynne of Woburn has long been mis attributed to the line of Edmund Wynne of London who never went to Woburn, MA.
I believe the author of the Cleveland genealogy made a huge leap in judgement and mistake when he associated the Woburn Wynne line with Sir George Winn and his father Edmund Wynne who lived in England during the same period as the emmigrant Woburn, MA Wynne.
As I recall the error may have orginated as there is or was a home in Woburn that had a form of the Wynne arms over a mantle - "three eagles vert. in a fesse".These arms have never been able to be attributed to any Woburn Wynne line who should have had a confirmation of arms or pedigree recorded by the College of Arms in England.The rolls of the College contain no Woburn, MA Wynne in the pedigree rolls for the period or any potential ancestor of the families entitled to bear these arms.
The assumption of the three eagles vert in a fesse by various Wynne's whether English, Irish or Welsh is because these arms were the arms of Owain Gwynedd, the first King of Wales and is the pre-emminent coat armour of all of Wales now assumed by the first son of the King of England when King Edward assumed the crown of the Prince of Wales some 600 years ago.
Since then every Wynne and variant seems inclined to make some claim to the Wynn arms whether legitimate or not in thier early family history.Keep in mind that there were at least 10 different Wynne families who had confirmation of arms that included some form of the coat armor of Owain Gwynedd.This may mean that the Wynne line of Woburn is connected to some other line of Wynne not associated to that of Edmund Wynne of London.
Also, your statment about the separation of early northern colonists from the southern colonists is not entirely correct.In an other line of Wynne we find that the supercargo for the entire American colony, Mathew Craddock (he was responsible for every bit of cargo shipped to the American colonies north & South) who married Damaris, the daughter of Richard Wynne of London
In my own line I have a nephew livng in the Plymouth colony and his uncle residing Jamestowne and Flowerdew Hundred, VA both ca 1619. Also there are Harwood's and Cary's who are cousins living in New England and Virginia in the early 1600's.
I think as you research further you will find the Cleveland Wynne attribution completely dis-proved just thought I could save you some work.