Broken Spirit/YMMV

Alas, Poor Villain: Discord, full stop. He nearly gets beaten to death in the first chapter, and it isn't pretty. He strays into Woobie territory when we learn about his past in Chapter 7.
Crowning Moment of Heartwarming: Discord and Fluttershy's interactions, especially in later chapters, are adorable.
Crowning Moment of Funny: Discord's pranks. He's constantly screwing with pretty much everyone.
- Fluttershy gets a few herself. For instance, her method for reprimanding Discord? Tickle Torture, with a feather duster.
Jerkass Woobie: Again, Discord. He's been through sheer hell, but he's not what you'd call "gracious" toward others.
Nightmare Fuel: Discord's injuries...aren't described pleasantly.
- Then there's the utterly horrible version of Discord in Fluttershy's nightmare. It's telling that when Discord comes into the dream and "saves" her, he's genuinely disturbed by the thing. It's also implied that this isn't the first time this has happened.
- Discord gets a severe case of blood poisoning in an early chapter, and Twilight suggests turning him back to stone as a last resort. Celestia immediately shoots the idea down. Her reasoning is that Discord may just die in the stone, or even be stuck in pain forever, unable to die.
- Then there's the basilisks. Sweet mother of God, the basilisks."
Tastes Like Diabetes: In-universe: Discord's view of Pinkie Pie. Naturally, she's the one who ends up looking after Discord when Fluttershy's out of the house.
Tear Jerker: Lots of 'em.
- Twilight's Heroic BSOD after nearly killing Discord is both saddening and a bit frightening, given how deep she sinks into depression. Luckily, she eventually recovers.
- Just try to read Chapter 6 without wincing. Poor, poor, Discord.
  - The entirety of the scene in Chapter 13 in which Discord comes to clean to Celestia about murdering their parents definitely qualifies Especially the ending of the scene.