Maryland Chancery Court Papers for 1804 and 1838 (listed in the Maryland State Archives website) also contain information on the Staylor family. John Staylor's father was Philip. He was married more than once. When he died, the children by a former wife filed a petition to obtain part of his estate. Those children were William, Mary, Catharine, Philip, John, Henry, and George.
As you know, John Staylor was born in Maryland. In his obituary, he was described as a "defender of the city in 1814." By 1830, he had moved to Virginia. He lived in Fredericksburg, where he was a tavern keeper and a butcher. The Fredericksburg historical records are easily accessed on the Internet. In the 1840s, Staylor also had a home in Richmond. In one census record, I recall seeing Staylor indexed as Taylor. I believe George Staylor also lived in Richmond. By 1850, John Staylor returned to Baltimore.
I ordered copies of the Chancery Papers, but I have not spent the time necessary to decipher them. The 1838 papers seem to indicate t that a Barbara Morrow (d. 1832) was the grandmother of the Staylor children mentioned above.
If you find out more about the families you mentioned, Please keep in touch.