Probably Rogue, assuming my PC/current-gen situation still isn't great. My first thought on seeing the new trailer was that it would be the Haytham Kenway game that 3 halfway-was, and that very much piqued my interest.
Now and Then, Here and There is a soul-draining experience that definitely qualifies, but I can't say any anime have really gotten me misty-eyed for a while. The last part of Wolf's Rain did it the first time I watched it, but then again, I was only 13 at the time.
I don't have much personal advice (as I'm going to college myself in the Fall), but everyone I've talked to has recommended renting books about a week into school, as some classes don't exactly use them heavily and you can find people to share books with for said classes. Good advice here!
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