DM: I do have one suggestion for what Twilight could be doing in the meantime, if you think it'd make sense.
Twilight Sparkle: Oh yeah?
DM: Getting all that alicorn magic under control?
Twilight Sparkle: Oh yeah! If I'm going to be fighting Tirek with ALL the other magic in Equestria soon, that's PROBABLY a high priority!
DM: You wanna resolve that with an Arcana check?
Twilight Sparkle: Sure! <roll> Ahaha! Haha... Great.
DM: No. You didn't. Now?
Twilight Sparkle: Yep. Natural 1. I'm not gonna get away with a quick, short-range teleport, am I?
DM: Nnnnnnope.
SFX: (PING! ^PING!^ PING!)
Discord: Oh, I forgot you had some wild west elements in this setting!
DM: Yeah, I really need to use more of it one of these days.
Your adapting a cartoon to represent a D&D session, natural 1's and 20's are perfect for explaining some of the things that happen. If it feels like you do it too much, its just because the source material you are drawing from has so many ups and downs.
It does feel to me like you use them too often (and maybe you could make some of them 2-4s or 17-19s. This page is a good example of a place to say she got a 5 or something, IMO, as I feel this result is FAR from the worst thing that could have happened here, even for a mage as experienced as Twilight). However, I’m not sure that feeling is because it’s actually statistically too frequent—I think it might be more that you often don’t call out the results unless it’s a nat 20/nat 1. If you said the roll results every time (often you just say “roll”) they would feel less common.
That’s kind of what Darths and Droids does (I think they also sometimes use roll results as “sound effects” accompanying the action, usually accompanying an attack, to make them not clutter dialogue), and they actually track the rolls they show to try and get a plausible distribution (https://darthsanddroids.net/episodes/0027.html).
Naturally, people forget that a natural 1 or natural 20 doesn't mean anything other than just a number when it comes to skill checks too. I.E. A barbarian, with a strength buff, high strength, and proficiency with expertise in athletics could have a +15 modifier; even a natural one means the check comes out as a 16, which against a DC 10, still passes, and quite easily. However, it's one of the most houseruled oddities that causes more tables than not to just make it 'super splendid' or 'fail horribly' regardless of outcome.
In a case like this, spud honestly uses the 1 a bit true to form: A failed arcana check would just have had nothing happen; however, Twilight's natural bonuses meant that she passed the skill to set it off (aka, a success), but the 1 means success with conditions. Much like how Fantasy Flight's Genesis system does, one can succeed with complications, or fail with advantages, to help spice up results (a method which I whole-heartedly approve of, as it adds narrative flair beyond the 'pass/fail' mechanic that the written rules cover).
But that's just the penny for my thoughts - given todays inflation, would it be dime for my time?
Yeah, it would have been nice to see her, or more of the buffaloes in general, in the later seasons. I've wondered for a while now why we never saw any at the School of Friendship.
She Does? It seems like her laughter is that sarcastic "Of course this happened" sorta laughter. Asking about the teleport seems like player asking DM to throw them a bone.
I like how Discord's player temporarily perks up at being reminded of the wild west stuff in the campaign setting. Just the thought of his sulking being interrupted for a moment because he's a fan of westerns and such.