In "The Hero" Wander is shown to want to rescue a princess to Up to Eleven levels. In "The Epic Quest Of Unfathomable Difficulty" Wander gets to save two princesses, but doesn't care about them at all! What gives?! He was too focused on saving the sock. (Or rather, the person who lost it.) He saved the princesses as required tasks on the checklist, not because they needed help.
Also, at this point in the show he'd already "kinda sorta saved a princess", so it could also be a case of 'been there, done that' on his part.
Also in "The Hero", it becomes apparent that Princess Demura saving herself is very fitting, as it's meant to set up Wander being a Foil to Brad Starlight. The entirety of the episode is about how life can't always go the way you want to. All Brad wanted was to fulfill his "destiny" of saving Princss Demura from King Drakor and 'living happily ever after'. Every step of the way, nothing in Brad's "prophecy" came true, and he doesn't take it very well. Whereas Wander simply wanted to save a princess. Despite that he doesn't get to save the princess, he's happy for Demura when she rescues herself.
Wander's attempt to pair up Dominator and Hater ends up adding a new conflict for Peepers to handle, in that Hater has become Distracted by the Sexy with Dominator's true form and has a fantasy about marrying her, while Dominator is the "greatest villain in the galaxy". From a writing point of view, this makes complete sense; Peepers has earned enough clout to manage Hater's conquests, and to invoke his boss's Flaw Exploitation to further his plans. Having to deal with his boss Looking for Love in All the Wrong Places will mess with his plans for universal conquest, and create more storylines for the rest of the season.
At the end of "The Cartoon," Dominator's choice of cartoon is revealed to be a Scooby Doo-like version of Gravity Falls. A perfect fit, given allegorically she's supposed to represent more serious narrative-driven cartoons (as opposed to the more episodic comedy-driven series like Wander itself), of which Gravity Falls is one of the more stand-out examples.
Why is Wander so confident about at first befriending Dominator and then setting her up with Hater? Because as "The Waste of Time" shows, he has spent years doing the same tricks to reform bad guys with kindness, if Major Threat is any proof. There is one problem, though; Dominator doesn't fit in the mold of previous bad guys in that she doesn't practice Pragmatic Villainy like Peepers or have a need to rule others the way Hater does. Hater craves power and companionship, despite his denial about the latter, but Dominator craves destruction and she doesn't have a conscience.
Upon first viewing it, "The Breakfast" would seem like merely a genius laughterfest utilizing the limits of animation. But on a closer viewing, by comparing Wander and Hater's morning routines are done, one notices how the happier Wander is proceeding with them with the help of nature and what it offers—showers with the help of a waterfall cheerfully, brushes his teeth with a pine cone, and does push-ups of his own volition—whilst the more miserable Hater has everything practically handed to him—Hater groans while using his more luxurious shower, uses his less effective electric toothbrush, and does only one push up after dressing in his workout attire. The same goes for the titular breakfast, where Wander makes a successful one while Hater, who has his breakfast made for him, ends up with nothing satisfying. Watching their attitudes during this, it's clear that Wander's successful day is attributed to happy-go-lucky, caring and positive—it would take effort to *ruin* his day. Hater, true to his name, is more negative and cynical, thus his day is going to serve him mutually. You can have all the physical advantages in the world or you could not; what determines the outcome of your day in the end is how idealistic you are. note To further prove this, when Wander and Hater get a half glass of juice, the former shouts" Half full" and the latter "Half empty"
"My Fair Hatey" and the songs "You're the Greatest" and "I'm the Bad Guy" are so well connected to one another it is brilliant. "You're the Greatest" was Lord Hater, in Part One, asking Lord Dominator's suit of armor questions about what things she likes so he can get to know, with the second part being how he declares, with immense development of his character, that she's the greatest. "I'm the Bad Guy" is essentially Lord Dominator's answer to Lord Hater's questions: she enjoys destroying planets, she enjoys destroying people's hopes and watching them cry, finds the villain business fun, and essentially gives a resounding "NO!" to wanting to date Lord Hater. On top of that, she roundabout acknowledges that she is "the greatest", in her mind, by calling herself THE Bad Guy, nailing down the coffin of all the romance tropes that Hater and Wander thought would work with her. Lord Hater asked a question, and he got an answer in spades.
"The Waste of Time" shows us that Wander is older than he looks. Word of God even states the beard he grows 50 years later is a fake beard he wears to appear old. Although sad, it could explain why Wander is so eager to keep making friends wherever he goes: so there will always be a new batch of friends with each generation.
In "The Legend", Wander's reason for not telling the kids he's 'the hero' becomes brilliant: the hero could be anyone.
Wander tends to be accompanied by banjo music, Hater by Rotten Rock & Roll, Emperor Awesome by Freaky Electronic Music, and Dominator by Orchestral Bombing (although varying wildly). This highlights their relationships: Wander keeps trying to get closer to Hater, as their instruments are similar. Wander doesn't even try to reason with Awesome, and they kinda just ignore each other, while Hater keeps trying to join Awesome. And Wander tries and fails to bond with Dominator, shown by how their music has little in common.
Elaborating on that, My Fair Hatey shows their character development with the music: Hater gets a much softer version of rock than usual, Wander switches to showtune music, and Dominator's usually dark orchestra switches to a lighter jazzy piece (while using many instruments in common with orchestra).
Heres one from the shorts. The reason the camera started glitching in, well, The Glitch is because Hater accidentally electrocuted it at the end of The Sharpshooter, the short right before that one!
It's likely he didn't intend this, but Doctor Screwball was a threat, since constant tickling can kill people due to their lungs not getting enough oxygen while laughing. He could have killed Sylvia, Hater and Peepers, and the entire population of Cluckulon had Wander not stopped him.
Wander at the beginning of "The Wanders" makes a good point in that he wanted to save the baby squirrel from whatever terrible thing was in the cave, so that nothing would happen to it. Being a baby, the squirrel's personality would be even more fragmented and underdeveloped, and Sylvia wouldn't necessarily have been able to invoke Flaw Exploitation the way she did when Wander's personality fragmented. That could have been Adult Fear there in trying and failing to save a baby from Cessation of Existence.
In "The Show Stopper," no matter how hard Peepers and Sylvia try, they cannot stop Hater and Wander's concert. Wander is the hero, mind, and one of the few times he's in the wrong; but Sylvia cannot reason with him or stop him by force. Just think of how dangerous Wander would be if he were like that ALL the time.
In the same episode, we also have the In Memoriam issue; which means Sylvia is confirmed to have murdered some of those drummers. And since the rabbit-people were seemingly too exhausted to run after watching a concert for four days straight, they didn't run when the bombs hit.