I believe I have found part of an answer for you:
Hester Barclay married Francis Bailey (1735 to 1818). He is found in the census in 1800 in Sadsbury, Lancaster Co. PA. source http://www.heritagepursuit.com/Champaign/ChampaignUrbana.htm and http://www.newphilosophyonline.org/journal/data/109b/Gabay_Article--New_Philosophy_July-December_2006.pdf
Also Maria Barclay married Judge John Young in Philadelphia in 1794 Source:
These two women were SISTERS to Hugh Barclay (1747-1807) of Bedford Co. since Hettie (Hester's) nephew was Josiah Barclay, Hugh's son who married Isabella Murdoch.
Also, Hugh Barclay of Bedford Co died in 1807. I believe thae the Hester Barclay who became the ward of Francis Bailey (and his wife Hester/Hettie) was probably Hester born 1801, daughter of Hugh Barclay of Bedford.
The 1800 census of Bedford Co. PA says Hugh Barclay had six sons and three daughters. Two of Hugh's known sons Samuel Moore and George W were born after 1800 --so there were others. I am trying to connect my Jacob Barclay, born 1804 and living in St Clair,Bedford Co in 1850 census to this family. The John Young family is also in Bedford in the 1800 census.
If it is true that Hugh Barclay of Bedford Co is the son of William (son of Hugh 1702-1764)and Elizabeth of Quarryville, Lancaster Co., PA, there is lots of room for a cousin relationship to your Hugh.
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