Alicia, Let me response some to your queries.
1. While my Forbes ancestor also have Sawyer ties I have not connected Jesse's Sawyer ancestors to mine.
2. So Alicia may have more than what I have on Jesse's line.
a. I know that his father Jacob Jr. had a brother Simeon.
b. Jacob Sawyer Jr. 1755-1827 also had a son Jacob Jr.
3. Jesse Sawyer and Caleb Forbes were close, they both are shown in various Court records.
4. In 1830 Jessee & Caleb came on horseback to present day Marshall County, IL in search for land.
5. They found high and dry land not subject to flooding like that in Camden & Currituck Counties. They returned to NC, sold their property. A 5 month 1100 mile wagon trip with a few other NC folk came back to IL.
6. Jesse and Caleb were neighbors in Marshall County.
It is late here so the rest will be very general from recall rather than records. In April 1845 Jordan Sawyer, son of Jesse, went to OR to find land. He returned and in 1847 captained a wagon train back to OR. Jesse and Jacob's brother Mark were part of the wagon train.
In 1850 Jesse is said to have died while on a ship to San Francisco (gold) and was buried at sea.
Some Illinois source talk about Jesse loaning money to a man (supposedly a preacher?) The man disappeared without repaying Jesse. The debtor returned and Jesse's wife, who did not know of the loan, welcomed the man into her home. Jesse returned later in the day and got some of his $.
Jesse was also friendly with the local Indians, more later..
Some of Jesse'