In the short "Ace in the Hole", Woody Woodpecker houses a desire to fly a plane...even though he had already demonstrated in previous shorts that he was already fully capable of flying.
Maybe he just liked the idea of being in charge of a machine.
Most people who drive cars can walk, doesn't mean they shouldn't drive.
In The Loan Stranger, why didn't the Loan Shark just try to get into Woody's house via the basement entry he had fallen into at one point?! (since he was going to eventually resort to breaking into the house anyways)