I spent LOTS of minutes doing this and feeling it was easily as creative and worthwhile as writing would've been. You're ace, you are. You should write one of those interactive adventure books.
I totally refer you to pp 239-240 of G B Stern's Another Part of the Forest (1941), which impresses upon me the essential stability of the relevant tropes.
Though you left out the sprained ankle/games match trope...
I can actually answer the two first questions more or less truthfully! Except instead of 'hilarious mishaps = wrong school' it was more like 'applied on a lark, got in and then had to go'. And I was a day girl.
The slightly scary thing is that I think all my answers are at least slantwise-related to the truth. I did go to boarding school, it was a family thing (though not a fecund family), we did have a midnight picnic on the beach ... etc.
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Though you left out the sprained ankle/games match trope...
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