William Penn was quite popular with some folks, but also had some problems with the Crown for the way the Colony was run.
He left the proprietorship to 3 of his sons, 50 % to John Penn, 25 % to Thomas Penn and 25 % to Richard Penn.
In 1746, John Penn died, and Thomas Penn became proprietor of 75 %, running the colonies 1746 to 1775. Thomas was rather unpopular with the colonials.
Richard´s son John Penn was an appointed governor of Pennsylvania, 1763-1771. Then Richard Sr. died, John Penn inherited 25 % of proprietorship and went back to England. His brother Richard Jr., who inherited no proprietorship, was appointed governor.
Richard Jr. was popular with the colonials and Thomas Penn was unhappy about that, so John was sent back to Pennsylvania.
In 1775, Thomas died, and his 15 year old son, another John Penn, inherited the 75 %.
In 1776, Governor John Penn stayed neutral in rebellion, doing nothing and letting the revolutionaries take over power. He evacuated from the advancing British forces, and eventually swore loyalty to Pennsylvania as republic. He got some compensation for confiscated lands.
This course of events depended on accidents of natural death and attitudes of individuals.
Could you get a course of events where the Proprietor of Pennsylvania, let´s say Thomas Penn dies in 1759, so Richard Penn gets 100% and John Penn is both the heir to owning the colony as well as the governor, sides with the colonists against King and Parliament in 1760-s to the extent that the Crown makes Pennsylvania a royal colony sometime after 1771 - while the ex-proprietor John Penn stays in Pennsylvania and Pennsylvanians rebel to get their Proprietor back?
This way, what would happen to the American Revolution if some colonies rebel to become republics, but Pennsylvania rebels to make Penn independent monarch?
Would USA have a union where most States have Republican Form of Government, but two are constitutional hereditary monarchies under Penn lords?