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Tearjerker: The Kingkiller Chronicle
The whole sequence where Kvothe loses his parents and his extended family.
And the following scene in the framing story, when Kvothe goes out to the woods and cries over the awful memory.
Kvothe's cruel stay in Tarbean
Particularly his father's lute being broken on the first day.
And Trapis, who's basically a heartbreaking moment on two legs. Think about it: He spends every minute, every day, every year on his bare feet in a cold stone cellar taking care of hundreds of homeless children - lonely, starving, defenseless, broken, hated children - giving them everything he has, which is so little it cannot be measured. Nothing he does can ever make a noticeable difference in the larger picture of the city, and the most he can ever hope for is to see the back of maybe one kid in a hundred who makes it out. Kind of makes you think there's good people in the world.
And taking a life-threatening beating,then almost dying alone in the snow on the equivalent of Christmas. And the only person to stop and help him is dressed as the worst of demons, and supposed to be out causing the worst of mischief, and he does it while a woman tries to drag him away to have fun.
To have fun and to not to be framed for the beating.
Kvothe crying about missing his mother in Auri's arms while he's under the influence of the plum bob.
The whole sequence after Kvothe kills the fake troupers is god awful. We get to see that one of the girls who has been raped four times a night repeatedly has caused her to be driven the next best thing to catatonic. Not to mention Kvothe's own reaction to them killing and impersonating a troupe is heartbreaking, you can just feel the sadness underneath the anger:
Kvothe: "You thought you could fool me?" I said, feeling my anger coiling inside me like a spring. "This is my family! How could I not know?"