[[WMG:Olive Branch is planning something with trying to get everyone to turn against Celestia]]
I mean, it'd probably make sense if there was some end goal for him to achieve other than "make the ruler look bad".
* [[spoiler:Jossed, see below]]

[[WMG:Said plan has to do with Discord]]
He's mentioned a few times throughout the story, and it could be considered foreshadowing... Also, Olive Branch is attempting to have a rebellion of sorts. And what do Rebellions usually cause? Chaos.
* [[spoiler:Jossed, his plan has to do with Immortality.]]

[[WMG:If this happens and Discord breaks free, he'll pull an EvilerThanThou on Olive and become the BigBad]]
He's also the last villain to have the Elements be used on, and one of Rainbow Dash's worries when she talked with Soarin' was that the Elements might have not worked, what with what happened before. It might be used to produce some final closure on that matter.
* [[spoiler:Jossed, see above]]

[[WMG:Alternatively, Olive Branch is doing this as a RoaringRampageOfRevenge against Celestia]]
Something must have happened during the Changeling invasion that caused Olive to become jaded enough to attack Celestia. Perhaps he lost a loved one?
* [[spoiler:Jossed, see above]]

[[WMG: Pinkie and Scootaloo's storylines will intertwine.]]
Specifically, [[spoiler: when Speedy Delivery is outed as abusing Scoots, it will cause Clyde to have a JerkassRealization in regards to how he treated Pinkie.]]
* [[spoiler: Jossed. Clyde had his realization shortly after Pinkie ran away, it just took this long to both track Pinkie down and work up the courage to admit he was wrong.]]

[[WMG: Olive Branch will be executed, as will [[spoiler:Speedy Delivery and Quick Delivery.]]]]
They are participating in a plan to overthrow the legal government of Equestria. If that's not high treason, I don't know what is.
[[spoiler:Now that they have assaulted and likely kidnapped a member of the extended royal family, it seems increasingly likely that they will end up on the gallows.]]
* [[spoiler: Jossed, they don't have the death penalty anymore. What Luna inflicts on Olive Branch could be considered AFateWorseThanDeath, while Celestia's to Speedy Delivery and Quick Delivery were more mundane.]]

[[WMG: Alternatively, they'll be banished...]]
''[[WebAnimation/TurnaboutStorm "Well that's not so bad compared to-" "To the moon... or even the sun."]]''
* [[spoiler: jossed]]

[[WMG: Alternatively he will get his wish]]
But it comes with some [[AndIMustScream consequences]]…
* [[spoiler: jossed]]

[[WMG: During the meeting with Celestia, Olive Branch will try to let the fact that Twilight tried to warn them be revealed]]
One of his arguments he presented in the beginning of the arc was the unexplained absence of Twilight, and people would start to ask questions about why Twilight appeared with the ''real'' Cadance (like where did she come from, what was she doing, what caused her to be there in the first place), so it's natural that at some point, Celestia or Olive Branch will mention that fact and this will be the lynchpin that Olive wants so much.
[[spoiler: Sort of jossed. He already knew about that and used it as blackmail against Celestia.]]

[[WMG: Rainbow Dash wasn't really bored by the ''Daring Do'' fanzine; it was just too soon.]]

[[WMG: The conspirators are Changelings]]
[[spoiler:When Twilight tried to scan one of the ponies to see if they were a Changeling, she gained a splitting headache... This could probably indicate that they're Changelings]]. Either they are Chrysalis' men who are enacting phase two of an elaborate plan (stage one is the Wedding, [[AllAccordingToPlan including her failure]]) to seize control of Equestria or a separate hive who are using the situation to their advantage.
* Actually, I think that that was part of a BatmanGambit -- [[spoiler: the conspirators (who are ponies) planned on Twilight using the spell on one of them, and cast a spell of their own to disorient her when she did, in order to more easily capture her.]]

[[WMG:There's more to the plan than just [[spoiler:kidnapping the Mane Six to use as hostages]]]]
In all honesty, Celestia would probably roast Olive Branch upon noticing [[spoiler:he has her student and her friends hostage]] so there's probably more to his plan than just "[[spoiler:Step down from your position of Godly Princess who can smite us with a single whim or we will hurt your pets!]]"
* [[spoiler:Nope, he was pretty much banking on her folding upon knowledge that he has them hostage... Didn't think that one through, huh?]]

[[WMG: Olive Branch will be defeated with an EngineeredPublicConfession]]
Specifically, the fact that he engineered Garble's gang's attack. I doubt he or his group will have much standing even among the GullibleLemmings if that knowledge goes public.
* Similarly, [[spoiler: Speedy Delivery's abuse of Scootaloo]] will also be exposed, causing him to be abandoned [[EvenEvilHasStandards even by other members of the conspiracy]].

[[WMG:Speedy Delivery and Olive Branch will [[spoiler:end up dead by the end of the story.]]]]
Wouldn't that be a satisfactory ending for those two [[SarcasmMode wonderful ponies]]?
* Well, I have been saying that I know a lovely Cupcake recipe that I would like to teach them...
** Jossed, unfortunately. [[spoiler:Celestia abolished the death penalty decades ago]]. [[spoiler:[[LaserGuidedKarma Fortunately]], he ''does'' get a FateWorseThanDeath in the form of a Penance Stare-like spell preformed onto him by [[GoodIsNotNice Luna]]]].

[[WMG:If the story continues after Families, it will proceed to deconstruct the {{Alternate Character Interpretation}}s of the Mane Six]]
Families deconstructed two popular fanfic ideas, Scootabuse and Tyrant Celestia and fitted them into the Post-Canterlot Wedding setting. Perhaps the continuing story may pick at Psycho Pinkie and Incest Twilight.
* Incest Twilight? Do I want to know?
** It's the WebVideo/FriendshipIsWitchcraft interpretation of Twilight's... behavior towards Shiny.
*** [[{{Squick}} Ugh...]] {{Deconstruction}} please.
** [=DarthLink22=]: I already have mentioned that interpretation. Chrysalis finds this [[EvilCannotComprehendGood the only logical explanation]] as to why Twilight came to her brother's rescue after he abandoned her. Outside that, I don't even want to touch this.
*** Ah; thanks [=DarthLink22=]. I feel better now.

[[WMG: [[spoiler: Discord's role.]]]]
It's evident the stories' theme is {{Forgiveness}} and [[spoiler: Discord]] in the Nuptialverse will be defeated once and for all when he's been forgiven despite the atrocities he's committed. Because [[GoodHurtsEvil it hurts him]] and [[PowerOfHate he gains his powers from everyone hating him.]] In the end, even [[ThisCannotBe he will go through a]] VillainousBreakdown [[EvilCannotComprehendGood why the others pity or feel remorse for him.]] With Twilight giving a KirkSummation.

[[WMG: Magical Mystery Cure will happen at some point, but it'd end with Twilight calling out Celestia for the crap she put her friends through]]
Or someone else.
* WordOfGod is that MMC won't happen in this universe (due to the author's own take on how ponies become alicorns). And even if the episode did happen, why exactly would ''this'' happen?

[[WMG: Chrysalis' partner in ''Direction''.]]
At the end of ''Families'', Chrysalis is directed to another agent of Discord's, to work on a plan to free him, and the first chapter of ''Direction'' has them moving ahead on it, though without revealing who this other being is. Possibilities:
* Trixie: Left half-mad by the Alicorn Amulet, she fled into the Everfree Forest. Perhaps Discord offered her a chance at revenge in return for her help, taking advantage of her insanity?
** Possibly {{Jossed}} by her actual appearance, which implies that she's unaware Twilight is no longer in Equestria.
* Sunset Shimmer: Just happens to show up and steal the Element of Magic right after we learn that Chrysalis and her partner are beginning their plan. Coincidence, or a DivideAndConquer strategy?
* Screwball: Popularly presented in fanon as Discord's servant. Perhaps [=DarthLink=] will deconstruct this relationship the way he has with so much else?
* Red Hoof: Immediatly after Trixie is purged of the dark magic making her evil, he grabs the device containing said dark magic (and even swings by Gilda's to drain the coin Trixie hexed to act as a calling card in case Gilda changed her mind about joining her) and makes a beeline to his 'superiors' in the Crystal Empire.

[[WMG: ''Direction'' will deconstruct EasilyForgiven]]
We have several characters who have been hit with this trope (Discord, Trixie, and Shimmer) and at least one of them has crossed so far into the MoralEventHorizon that forgiveness isn't an option.