Dave Cain & I have corresponded on the above line--2nd ggfa was James Henry 1825 s/o Caesar & Jane Joughin s/o John 1759 & Eleanor Wattleworth, s/o Jon bd? & Jane Quiggin.
It would seem that Jane is the 2nd wife of Jon, md Dec 1754.
If Jon is the one who died 1766.left will, he might have been married #1 to Ann Mylchreest 1716 & fathered at least 3 daughters 'by a former venter': Joney (wife of Silvester Clark), Margaret (wife of William Cooile) and Catherine (wife of Thomas Killip)--mentioned in the 1766 will. Ann Mylechreest Caine died 19 Aug 1754 & left a will 1754 which seems to nicely fit our information
1754-3 E w CAINE Ann McYLCHREEST d 19 aug 1754;ch margt,jony,cath;husb john exor;gson john clark;inv
Hopefully, the path to Jon is somewhat clear. From him backwards, it is quite murky.

Which of the many many German Cain(e) lines does Jon belong to?
Goodwin thought that our Jon was either the son of Henry Caine 1671-1711 or son of Henry Jr
There is no explanation as to why he selected the father being Henry. He also was overwhelmed by the number of John/Jons and the many children fathered by John/Jon--of course the parish records of the time didn't often mention the mother.
According to him, Henry Caine Sr was md Catherine Mylechreest 1 Jun 1701 German--they had
Henry 1702
Matthew 1705
John 1707
Mary 1709 md Wm Lace
James 1710 md Isabel Radcliffe--I don't think this one is correct

Is there a connection between Catherine Mylchreest md Henry and Ann Mychreest md John?
What, if any, is the connection between Henry and John?

Of course there are way too many John Cain(e)s in the general time period. It has been many many yrs since I first ran across these folks and I'm struggling to try to clear a path for Dave, who lives in Italy.

Goodwin also added a note that, if true, doesn't help clarity.
"as related by Jas Morrison of Peel. One day John Cain (J.H.C. who died 1908) came in to their house and said he had a violent quarrel with his father. And said that his father had no right to Ballgyr and that his branch of the Caines would die out for want of an heir. Many years ago, one of the Caines, the heir, had a quarrel with his father and struck him down. Seeing his parent lying unconscious and thinking he had killed him, the son fled from the Island and was never heard of afterwards. But if he left descendants, they and not the present holders of the estate were the true owners.
The writer had heard something (a long time back) that the recent Cains of Ballgyr had not a clear title to the farm. Be as it may, the young Cain who ran away would almost certainly have changed his name and if married would have been married under the assumed surname--his wife and children, if any, would have lived in ignorance of the true state of affairs".
I did the best I could to read the above & to type it as written by him.
Just adds more blurring!

Hopefully, some of the genealogy sleuths on the Board can provide some help.

Thanks,
Donna