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Judith, oddly enough I was in Fair Haven today, and if I'd known I would have tried to verify this Simeon's identity for you. I don't get there often, I'm sorry to say.
Although I can't give you the proof you need, I can give you some data that may lead you to your proof. I think you are on the right track. First, Fair Haven VT is on the border of Washington Co NY. Hampton NY and Fair Haven are contiguous, and Whitehall NY is just beyond. So, that is why people from this area seem to be from both NY and VT -- the lines blur.
Second, the elder Simeon Osgood was born in Whitehall NY (a few miles from Fair Haven) in 1784. Simeon 1784 is mentioned in his mother's bible (The Susan(na) Stowe Osgood bible mentioned here before), and in his father's 1851 estate. I believe I have found him in the 1840 census in Livona (Livingston Co) NY and in the 1850 and 1860 Concord (Erie Co) NY census. If you spot these locations on the map, you'll see that Pittsburgh PA is not that far away. I do not have the names of all the children, but do have a Charles b 1828. If Simeon Jr. was born ca 1820, they could be brothers.
The only other interesting info I have about Simeon (the elder) was from a bankruptcy file in Washington Co, ca 1831. Simeon was the major creditor of one his brothers, and when the brother filed for bankruptcy, Simeon got his brother's property, instead of payment on the debt. At least it shows that big bro Simeon was supportive of his younger sibling. It also places Simeon still in Whitehall ca 1831.
Hope you can prove your Simeon as Simeon Jr.; let us know if you do. The dots seem to connect.
Carolyn
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