Obadiah's wife shown as Anna (b. ca 1793 England) on 1850 Census (New Hartford, Oneida Co, NY) and as Hannah (b. ca 1799 England) on 1880 Census (widowed, living w/ son Charles, Lenox, Madison Co, NY). Based on birthplaces for their children, they emmigrated from England ca 1839. You may be able to find an immigration record - (not an area I'm familar with - sorry).
Charles Bosworth's wife was Charity Sabins (b. ca 1846 NY). The clue is her sister Rhoda living w/ them 1880 Census. This leads you to the 1860 Census for Fenner, Madison Co, NY, showing both Charity and Rhoda (& 3 siblings) with their parents, Sherwood T. Sabins (b. ca 1817) NY and wife Betsey (b. ca 1823 NY).
Re Winn line - Have you checked for a Union Army record for Hiram? He is the right age. Maybe he (or Sarah) filed for a pension later. If I come up with any great ideas on the Winn line, I'll post it.
Hopefully that helps. Sounds like you are local - you might check at the Town of Sullivan Historian's Office (north of Chittenango on Lakeport Rd) - they might have info on the school house (maybe even a picture) and something in the family files as well. Not sure who is the historian now - last I knew it was Carol Greene 633-5344 (H). The office used to be open on Wed. afternoons.
Cheers.