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You can reasonably argue any one of them, really.
Fluttershy would be easiest because she'll accept anything graciously.
Fluttershy would also be hardest because she A) won't tell you upfront exactly what she wants unless you really bug her about it, and B) she'll accept anything graciously; you'll have a hard time knowing how well you've chosen a gift unless you've really, really, really impressed her.
Twilight would be easiest because she's a bibliophile. Just get her an obscure or rare book.
Twilight would be hardest because while the obvious gift (a book) is there, she's also ridiculously well-read and chances are high you'd get her a book she's already read. She also doesn't have too many personal interests outside of books and magic, and the giving the latter...I don't even know how that works.
Interrupting with 'Ternal post because of relevance.
Applejack would be easiest because she's very polite and will therefore accept anything you give her that's reasonable. She might ask questions, unlike Flutters, but she'll take it. If you ask her what to get her, she'll probably have no qualms with telling you exactly what she wants.
Applejack would be hardest because she's not a particularly material pony apart from her hat and hairties. Assuming that the gift we're giving has to be material (as we're shopping), your best bet would be to find something that she needs for the farm. On top of that, AJ places a lot of value in sentimentality (her hat, Bloomberg, etc.), which isn't something you can buy from any store.
Dash would be easiest because Wonderbolts. Get her an autographed something, done.
Dash would be hardest because, like AJ, Dash is more about athletics than possessions, and what possessions she does have are mostly stuff she made herself from the weather (cloud palace, cloud beds, etc.). Your best bet would be getting her something that improves or enhances her flying experience somehow, without getting in the way.
Rarity would be easiest because you can either get her something fashionable/trendy, or just get her high-quality materials. Even if you don't do well, Rarity is classy enough that she'll accept it, albeit likely with some hesitance and many "Ehhhss".
Rarity would be hardest because her tastes are so volatile. Something you get that's trendy now might be lame by the time she gets the gift.
Pinkie would be easiest because sugar. Get her anything that has sugar in it, and done.
Pinkie would be hardest because while she does spend a lot of time baking or whatever, what really makes her happy is making others happy, and how do you give that as a gift? You can't tell her "I'll just be happy for today" because then she knows you're faking.
There's aspects of each that would make it hard, and there's aspects of each that would make it easy. I could've put a lot more thought into some of the above, but suffice to say, there's plenty other reasons why each would be the hardest and the easiest.
No point explaining it unless someone wants to know, and I can do that in a PM.
Oh God.
I jungled Maokai once. He's all right, but I would really like to know why I don't see more Maokai's abusing the Sapling/Twisted Advance combo--tossing a Sapling over a wall to gain vision on jungle creeps or a champion, then using that split-second of vision to Twisted Advance to them.
Fix'd.
[Spider Dance - Toby Fox] [♫] [t] [Splinterfox | MW/BM | Tanaris-NA]
[OSaS A1 ~ 80% Completion] ~ [Thank You, MLP] ~ [ ??? ]
Sig: Elyssia | DJoron is the Best
Sig: Elyssia | DJoron is the Best
Sig: Elyssia | DJoron is the Best