The Shadrick Penn who married Ann Cheney was NOT the son of BENJAMIN Penn Sr as you state.He was the son of JOHNPenn, another son of Edward and Judith (Deavour) Penn.
Three of Dinah and Benjamin Penn, Sr's eight children came from Maryland to Kentucky - Benjamin Jr. (my line) settled in Franklin and Henry Cos KY, Joseph settled in Bourbon Co Ky and Shadrach settled in Scott Co KY.All three were in the Revolutionary War.
Shadrach Penn, son of Dinah Acton and Benjamin Penn, Sr., was born in 1750 and died in 1831 Scott Co KY.He was married twice.By his 1st wife (name unknown), he had two children and by his 2nd wife, Margaret Holland, he had seven more children.
Shadrach Penn, son of Elizabeth Waters and John Penn (John was s/o Judith Deavour and Edward Pann), was born ca 1754 in Baltimore, MD, married 1st 15 May 1779 in Baltimore, Ann Chaney, and had a son Francis.Shadrach then moved to Ohio, where on 22 Aug 1809 in Ross Co, Ohio, he married his 2nd wife, Elizabeth "Jenny" Cross.They had 9 more children (Ameziah, Samuel, Caleb, Fannie, Nancy, Sarah, william, Hanson, Jerome), some of whom moved to Pike and Adams Counties in Ohio. Shadrach died about 1834/1840 Jaybird, Adams Co, Ohio and is said to be buried in the Old Smalley Graveyard.
There were several Penn men by the names of Edward, John,Shadrach, and Benjamin, so it is very hard to keep them straight.