I am not as prudent about checking message boards as I should be. I saw the Winn geneology you posted and was very impressed. Several questions popped into mind. Jacobs birth date and Simon? Simon's lists his parents as Joel and Betsy. He was Webster's father and Adelaide's husband. He owed land next to Chancey and John but I have never been able to connect him to the family. Issac's will does not list him ( Issac had no issue and was a widower so his estate was divided up between living relatives). One newspaper article from Chauncey's daughter states Jacob came over from England with two or three brothers. I thought Joel might be a brother. He states he was born here but Simon says he was born in England on some sources. I don't know if there is a connection or not. Simon moved back to Canada for a while before returning to Wisconsin and dying there.
I contacted come of Jacob jr family and they said he died of fever on board ship.
I contacted Stanstead but was unable to find out any information on Jacob's death and/or burial. It has been a while since I spke with the Stanstead people so maybe I will try again.
If I can help fill in any more blanks I will be happy to do so and promise to check my messages more often.
Thanks for all the good work!