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One of the Hogwarts founders was from Milo's world.
Consider:
  • Hogwarts is considered weird even by the standards of wizards. If it had some Wizard magic, that would explain it.
  • In chapter 52 (CC Chapter 19: The Boy Who Didn't [1]), we clearly see that the Sword of Gryffindor is a Vorpal Sword ("Snickersnack!"). This means that the founders must have somehow had access to D&D things.
  • In Chapter 58 (SD Chapter Five: City of Light [2]) Lucius confirms that the ritual used to summon Milo "seems to only have been used once—twice at the most—in all of history". In other words, he confirms that the ritual has been used before.
A simple explanation for all three of the above facts would be that one of the founders was from Milo's world.
Fiona will find Milo's old spellbook.
Since anyone from Milo's world can become a Wizard as long as they're intelligent enough, there's a chance Fiona can learn how to cast spells like he does.
  • The author said that people from Milo's universe and people from the Potterverse are essentially different kinds of human and "follow different laws of the universe" in the AN at the top of chapter 23, but he might have been referring only to the the whole game mechanics thing. He also said that Milo was closer to a muggle or squib than a Potterverse wizard, so it could go either way...
Lupin's lesson with the boggart will go worse than in canon.
The boggart will see Harry and take the form of Voldemort instead of a dementor, since Milo was attacked by one instead of Harry, and Lupin will have to step in.Or it will see Milo and take the form of a Phantasmal Killer, and Lupin will have to step in.
  • Milo could also see it as half a dozen other horrifying things: demons, fae, horrifying Far Realm Abominations, or even that vision of himself he saw in the Mirror. Who knows, he might try to fire some attack spells at it, and cause some collateral damage.

Milo will make amends with Harry after the first Quidditch game in the 3rd year.
After Harry is attacked by the dementor and falls from his broom, Milo will use Feather Fall to slow his descent. He may also be able to repair Harry's Nimbus 2000 (which is broken by the whomping willow) with magic, since it doesn't register as a magical object by Milo's standards.

Fiona and Milo will become allies.
They're not exactly on the same side, but they are both trying to determine how a mysterious-to-them world works.

But mostly, I want to see the looks on the Obliviator's faces when their Obliviates inexplicably fail on this already-too-persistent Muggle.

Confirmed!

The wizard Lucius was trying to summon was Mordenkainen.
Powerful ancient wizard who could revive the dead (and is willing to side with Evil if Good is looking too strong)... with the same name as a certain rat familiar. Don't ask how Mordenkainen would become "a great mythical wizard mentioned in ancient texts" on earth..
  • All but confirmed in Chapter 63, with an oblique reference to the Circle of Eight
  • There's some more support for this one, actually. First, Mordenkainen has made trips to Earth before, documented by Muggles, no less. Second, it is established (Chapter 61) that someone in physical contact with the target of the summoning spell, as Milo would have been with Mordy, gets dragged along as well. We also see, in Chapter 62, that the summoning literally requires the name alone, no description added — and way back in Chapter 58, Lucius confirms that they summoned the great wizard "by name." It gets worse when you realize that, had Milo and Mordy not been in physical contact when the spell hit, and that given how them being on different prime materials affects Mordy, Lucius' arrogance almost got him to exchange Bellatrix Lestrange for a common garden rat.
  • There's even a reason why Mordy was targeted instead of the archmage Mordenkainen - when we see Lucius attempt the ritual again, we see that it requires a 'secret never spoken aloud.' Everyone uses deeply personal secrets... except Lucius, who uses something he'd never said aloud not because it was terrible or embarrassing, but because it was irrelevant and minor. In other words, the DM of the Potterverse, which has been repeatedly shown to be less inclined to gaming the rules than Milo's world's DM, intentionally got him back with Exact Words

Everybody is a PC
It would explain why Milo keeps getting pulled out of his timeskip whenever something interesting happens and he's not around.

Milo will get around Prestidigitation's limits by talking to his Professor about Conjuration
There's a fundamental difference between Milo's Conjuration and Potterverse Conjuration. Namely, that for Milo, Conjuration is an entirely different School from Transmutation, while for Potterverse wizards it's an outgrowth of Transfiguration, i.e. turning "nothing" into "something". Thus, the following can easily play out.
  • Milo becomes frustrated with Prestidigitation's limits and decides to cheat by using Sleight of Hand to replace his matchstick with a small, crude, obviously artificial, and fragile pin he creates using Prestidigitation.
  • He fails the Check and McGonagall sees him trying to switch them out, then asks where exactly he got such a poor pin.
  • He truthfully tells her he created it, whereupon she reveals that he properly shouldn't be able to, as that's much more advanced magic than what he's been failing at, as match to pin is first year, but Conjuration is sixth year at least.
  • Milo says no, creating the pins (or anything smaller than six inches, really) is quite easy, even if he can't get them looking right.
  • The two of them have a conversation about Conjuration and Transmutation versus Transfiguration and Conjuration. McGonagall is thereafter very understanding of Milo's creations and wholly relieved at having finally identified Milo's "mental block".

Milo will be absolutely horrified once he learns that people in Harry's universe can forget skills
Without practice now and again to stop from getting rusty, Potterverse wizards naturally forget things over time. In Milo's world, Characters can only forget Skills by deleveling, regardless of time elapsed. It would therefore by terrifying to learn that all his friends gain negative levels for essentially no reason at all.
  • This has the additional benefit of Milo finally discovering the mitigating factor to Potterverse wizards to correct their unlimited spell list, at-will, no-saves magic for game balance. Maybe now that he understands the price of their power, he won't be so quick to feel inadequate.
  • Confirmed as of Chapter 13 of third year. However, he's quick to observe that this could work in his favor if the Death Eaters should ever think of a plan that requires him not perfectly remembering minutia from years ago.

Milo will get around his inability to use the same magic as everyone else by using his Craft Wondrous Item feat
We know this feat makes it possible for him to create items which contain spells that can be activated, and in order to create them the spells in question have to be cast in the vicinity of the item. However, nowhere is it stated that the spell in question has to be one of his world (because there are no non-D&D spells in D&D), and someone like Hermione would sooner or later take interest in it and ask him about that, making him at least try.
Sure, they would probably be specific spells—like a transfiguration spell that can only change a match into a needle—as opposed to a do-whatever-you-want-with-it transfiguration spell they have—but it's a start, and for someone with a limited number of spell uses per day even those few extra uses of situation-specific spells can help. Not to mention that he does have resources (experience from whatever source, and a lot of salt to pay for it).
And when the specific effect is "throw the object you are pointing at out of the hand of whoever holds it" (expelliarmus) or "incapacitating the enemy" (petrificus totalus, stupefy, etc.), there's no doubt they can be useful. For the added effect, he could have them be sticks that appear to be wands—those don't weight much and thus he could fit a whole lot of them in a pocket or two.
Because after all, he doesn't need to multiclass as Wizard/"wizard"—he merely needs to be able to use some spells which those with the class "wizard" can use.

Milo has become a GMPC
Because what else do you call a PC without a player?
  • A disaster waiting to happen, that's what you could call them.

The DM of the Potterverse is J.K. Rowling.
It's been shown that more blatant abuses of game mechanics aren't tolerated in the Potterverse (such as the wood-to-quarterstaves trick, or the lasting consequences of trying to access Cleric Divinations), and Milo tends to drop out of timeskips for flavor reasons, rather than mechanical ones. Rowling is irritably tolerating his presence in her story, but she had a plot in mind, and the more he mucks with it, the more she forces him to develop into a reasonable character, with motivations more fitting a work of literature, rather than a tabletop campaign.

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