While I don’t agree that I’m unaware of the respective framing of both movies the plot device attempts to run his character ascent in the same manner and to do that a reset of sorts is necessary. It illustrates that any change is not persistent and therefore devalues the character shift. The aspects you raise are trivial and don’t debase core elements of character, in my view anyway.
There is not a digression of his character in play in either of the situations being discussed, so nothing is "devalued".
He lets cynicism guide his life because the woman he loved and the man he'd seen as a father figure turned on him, and later goes back to trying to be the "carefree scoundrel" after his son fell to the Dark Side, but neither of those things change who he is on a fundamental level.