These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Dork Age: Sometime around the 1990s, the Skull openly denounced Nazism, supposedly because it was getting old-fashioned: In the future, he'd be a much more dynamic villain. In other words, the guy who had previously spent most of his adult life fighting fanatically for Hitler's dream suddenly and for little reason threw it all away, in order to indulge in pure, sadistic For the Evulz villainy. Later characterizations have since reverted to the Nazi Skull, though there's still considerable flip-flopping on whether he's primarily a Nazi Tautological Templar or merely a crazy sadist scumbag who likes Putting on the Reich.
A recent miniseries by Greg Pak heavily rewrites the Skull's original origin story, which was substantially based on the real Hitler's early life, and attempts to establish him more firmly as The Sociopath, among other things showing him as a mass murderer and Knife Nut long before he became the Red Skull. Fan opinion is divided on whether this is a good thing.
Executive Meddling: Mark Waid wrote a story narrated by the Skull, very much from the Tautological Templar perspective, in which the Skull self-identifies as an embattled and unappreciated defender of the future of the white race against the rising tide of color. It's very much Deliberate Values Dissonance, as the story quite blatantly showcases his Moral Myopia and paranoia, and meant to show how delusional he has to be to consider himself a hero. But somewhere along the way, the studio execs still got cold feet and ordered a full last-minute rewrite to remove the self-justifications and increase the cackling villainy, resulting in an utterly Anvilicious final product. See here for some elaboration. Eventually, the original version was published in a collected edition.
Hilarious in Hindsight: The original inspiration for the Skull? Joe Simon saw a hot fudge sundae shaped vaguely like a human torso. He'd originally planned a villain called Hot Fudge until he realized the cherry looked a lot like an exposed skull. So...
Moral Event Horizon: As a young man when he murdered a teenage Jewish girl for rejecting his clumsy and creepy advances, even though otherwise she liked him and was willing to overlook it. He thought it was the best rush of his life and it served as a release for all the pent up anger and frustration he felt towards the world. One of the reasons he joined the Nazis was for more opportunities to have a rush like that, and it still serves as one of his prime motivations for his numerous crimes.