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I'm really enjoying the fairly slow piece-by-piece transformation you two have, and the sequence you've put together, Annon, is miles better than Twilight's sprite changing with a click. Thanks to both of you.

https://pastebin.com/nLd6mg7g
Finished up three more of each, for a total of five normal and five bimbo. I've been struggling to find much of a "voice" for bimbo Cheerilee so if anything stands out, let me know.

Ah okay. I had only thought of running them by you for approval, and not actually to put effort into them in yet. I've done an example of another trivia question as a warm up, so if you see anything wrong with this, let's work it out. Otherwise feel free to use it.
https://pastebin.com/QghfQiX6

I'm leaning hardest for option 3, but her clothing and body changing together over the bimbo levels. So like once her breasts become large enough to render her school jacket useless to cover up anything she'll go without, or her skirt becomes short enough so she can show off the full length of her stockings so she starts wearing them longer. As for her hair or accessories, I'm pretty neutral on those, although I do like the look of the huge top-right ponytail.

What quote is commonly attributed to Socrates?

    - I think, therefore I am. (False, actually Descartes)
    - I know that I know nothing. (Correct!)
    - I am what I am. (False, actually Popeye)
    
What is change in acceleration over time is called?
    - Speed (false)
    - Jerk (correct)
    - Shake (totally false)
    
What is the element of a color that refers to its brightness?
    - Hue (false)
    - Tint (false)
    - Value (correct)
    
How many sides would a basic tetrahedron have?
    - Four (correct)
    - Twelve (false)
    - Eight (false)

I'm having significantly more trouble thinking of bimboized versions of trivia, but it's a start:

What size would a DDD cup bra actually be?
    - G cup (correct)
    - H cup (false)
    - Trick question, it's still an D cup (false)

Ahh yeah that does make my idea not make much sense. I guess I'm just kind of a sucker for those "gotcha" moments.

As for the formula, I think it could also incorporate the player's stats in some way, adding them to the number they need to reach for an h-scene. This would represent the player character's personal attractiveness to the girl, as opposed to bimbo level (how open they are to sex) or their s-link level (how close you've become). You could also put a hefty negative modifier on the required number if you get either bad end, pretty much requiring you to bimboify them (or boost your stats)

I was thinking that you could have a fake out h-scene, where one of the more suspicious girls (perhaps after you've bimbo'd half their friends without building her relationship beyond a "hello") tries to seduce you. If you fall for it, she'd become indignant/furious, and unavailable to spend time with until you manually increase her bimbo to loosen her up. This might be something to implement much later, once the main paths are set in place.

As for when to normally get lewd, I'd say after or right before successfully maxing out their s-link, since they'd want to open up to the person that helped them so much. Maybe for the first h-scene you can "convince" their bimbo level up slightly? If they're bimbo'd first or early, maybe you can start h-scenes halfway through the s-link, as a way to get their bubbly minds off their troubles, although it'd take the place of actually progressing the relationship as a price (i.e. no progress bonuses from the conversation).

By the Book: Bimboification
Arcana Whores (a little too vulgar?) (I like the persona ref though)
Arcana Girls: Major Changes
Mastering Canterlot High
Master of Studies and More
Todd Howard's Wild Ride
Shaping the School's Future
Change: Power is Yours

I do like Airhead Academy though.