The Hooded Claw is motivated not by money, but by contempt for female beauty.Penelope is a woman like no other: beautiful, athletic, trusting, highly intelligent, and strong enough to stand straight while holding a baby camel. Sylvester Sneekly became her guardian against his will; the sooner he's rid of this beauty he finds so repulsive, the better for him. So as the Hooded Claw, he plays on Penelope's one weakness: She's fooled by even a Paper-Thin Disguise.
Penelope and Sylvester are lovers, and her "perils" are S&M roleplaying. They are both enjoying her inheritance money with their travels.This one sounds so wrong, but feels so right.
Sneakly/Claw is Uncle Arthur from BewitchedDerrwood and Sammy get boring after a while, and pranking Endora has real hazards; so he sets up an Alternate Universe based on his fave silent 'damsel on railroad tracks' films and casts himself as the most interesting character—the villain. Tabitha and Adam had Wacky Races on, and Arthur saw the cast he wanted.
Penelope Pitstop is Princess PeachBoth are blondes who are quite smart but often get into trouble and knows several little guys who would do anything to keep her safe.
Penelope Pitstop is a Mafia Princess.The Anthill Mob are still carrying out her late father's orders to guard her as some sort of Mafia Secret Service.
Clyde has some sort of crush on Penelope Pitstop.But he'll never admit it and it'll most likely go unrequited anyway.