Looking at "Our Man Bashir" with the knowledge of what is going to happen, he concludes that Bashir isn't being his fantasy self, but his real self.
He has a truly fascinating theory that introducing Starfleet to the Borg was a move on Q's part simply as his ultimate argument against Picard's insistence that Rousseau Was Right, given that it ultimately results in Picard's purely hate and revenge-driven actions in First Contact.
Picard: And I will make them pay for what they've done!
Chuck: And somewhere... Q is laughing.
That Picard's enraged reaction to being told to destroy the Enterprise-E in First Contact is because when he loses a ship, such as the Stargazer and Enterprise-D, he takes it as a personal failure. The Borg, who have taken so much from him, who for the six years he has had to live with that personal failure, that they beat him, that he wasn't good or strong enough, will not be the ones responsible for him having to sacrifice the Enterprise-E.
Also note that the ship in his display case that Picard broke in his moment of rage is the Enterprise-D, fitting Chuck's theory that Picard hasn't gotten over that loss when he reacts with shock to it.
The reason the people in "Regeneration" turn into Borg so much slower than before is due to so many of them being assimilated by only two drones, thinning out the drones' nanoprobe supply. Though this ends up not working out when one of those same drones assimilates an entire computer mainframe in seconds.
He has some pretty compelling musings that the two species from the infamous "Dear Doctor" evolved into the Breen and the Pakleds.
In the "Dark Frontier" review, he explains that Starfleet's rudimentary knowledge of the Borg came from the El-Aurian refugees, and the incomplete notes of Dr. Phlox from before he was gunned down by Breen assassins, more than likely out of revenge.
He makes a good (if half-joking) argument that, despite The Worf Effect, Worf still represents an improvement in heading up security on the Enterprise-D, considering that in some first-season episodes security never seems to turn up at all!
He's also mentioned that Worf's gruff summaries of situations are frequently the correct ones and cut to the heart of a problem the other characters are dithering with.
There's also the theory that the Effect occurs because the command staff are so busy screwing around that when it comes time to fight, the enemies have had a chance to prepare for Worf.
That The First Doctor from Doctor Who had his first moment of Character Development when Ian Chesterton stopped him while he was considering bashing an injured man's skull in so he could escape from danger. He realized how desperate and cowardly he had been in that moment of weakness, and that a lowly Human had acted far more noble than he had been. The reason The Doctor's companions are mostly human from then on is because he realized Humans Are Special because they stop him going too far. This also nicely explains why he loses his cool so much when humans don't measure up to the standards he knows they're capable of.
The different actresses playing the Borg Queen are explained by the first model being replaced after her failure in First Contact, then given another chance after her successor developed a destructive obsession with Voyager.
Particularly weird is that Chuck makes no reference to this being his own theory, and just throws it out like it's canon.
Chuck goes out of his way on numerous occasions to point out that it's the opinionated guide. It's entirely possible that this time, he figured it should just be taken as a given.
"Before and After" features him stacking up the evidence that the Ocampa were actually genetically engineered as a race of sex slaves. Except for the body temperature, but the rest is damn uncanny.
His more accurate alternative to the Star Trek Movie Curse: each and every bad Trek film is heralded as bad when the main characters sing (the infamous "Row, Row, Row Your Boat" singalong in V, Data's "Life Forms" song in Generations, Data and Picard doing HMS Pinafore in Insurrection and Data singing "Blue Skies" in Nemesis).
The sole exception being The Motion Picture. Because it would "detract from the boredom".
In "Ship in a Bottle," Moriarty erroneously refers to Sir Arthur Conan Doyle as an Englishman because he was unhappy with Doyle for writing him as a villain.
In his TNG Look-back at Reg Barclay, he points out that he and Seven are very similiar personality wise, both like self-aware holograms, are introverts, brilliant problem solvers and both experienced (while extremely different) a form of higher conciousness integrated with technology. Leading Chuck to Crowning Moment of Heartwarming Fridge Brilliance.
Chuck: "You know with all the Chakotay romancing in [Human Error], it's intersting to think who might actually the most compatible with Seven. And I think it's Reg Barclay."
That the Voyager episode "The Void", made close to the end of the series, represents a look at the show as it should have been from the start, dealing with supply shortages, moral dilemmas, alliances with shady characters and Neelix actually being useful(as well as bringing up his original occupation of scavenger, even if it wasn't put to use).
Kyoko of Madoka Magica made a wish to help her father prosper, which in turn allowed her poor family to have money for food. The reason she is always eating is that she has a disorder that helps her cope with despair, because having a full belly reminds her of happier times with her family before everything fell apart in her life.
In Booby Trap of TNG, Guinan says she's attracted to bald men from a time when one helped her when she was hurting. Cue Chuck throwing in a clip from "Time's Arrow" where Picard helps an ailing Past!Guinan.
In "The Killing Game", speculates that the reason for the World War II scenario is because the head Hirogen recognises the parallels between the Hirogen and Nazi Germany. Both groups have technological superiority over their adversaries and a love of conquest, but this will ultimately prove their undoing, as they simply do not know how to hold the ground they've taken.
Similarly, the reason the Hirogen are not aware of the Borg despite being spread out throughout the galaxy, is because their ships rarely hunt with any backup, ironically making them easy pickings for the Borg to assimilate.
In "The Bonding", Chuck speculates whether its original premise, of a young boy creating a holographic recreation of his late mother, helped inspire "Hollow Pursuits" later that season, in which we are introduced to Reg Barclay, who constantly retreats into holographic fantasies.
Voyager apparently records the brainwaves of all its crew members all the time.
In "Meld" we find out that apparently its just so easy to turn off parts of someone's brain...
His review of "Emissary" points out the true horror of the battle of Wolf 359, only glimpsed briefly in "The Best of Both Worlds" left people such as Ben Sisko deeply affected having lost loved ones to the Borg.
Most especially the instances where Chuck's version of Janeway is less extreme or psychotic than the cannon Janeway, such as in the the one-off My way or Janeway segment.
He also manages to make the Idiot Plot that was Nemesis make a surprising amount of sense by having it be all part of Janeway's plan to take over the Federation and the Romulan Empire.
In "The 37's", Janeway momentarily considers having Voyager's crew settle down in the human settlements built by the titular character's descendents, reasoning that it's the closest they'll come to Earth for a long time. Rather unsettling how she ignores the numerous members of her crew that aren't human and thus don't hail from Earth at all, isn't it?
In "Innocence," Chuck speculates that the more rational explanation for the children disappearing, is that they are simply being murdered and the crew of Voyager are gullible morons for just accepting the whole "our race ages backwards and turns into energy" explanation, without any proof.