YMMV / The Life And Times Of A Winning Pony

  • Nightmare Fuel: Rainbow Dash getting increasingly aggressive and incoherent after receiving one blow on the head too many.
    • What it's implied was done to Nimbus Gust before she died. Her body is implied to be badly mutilated, and Chrysalis later reveals that she glued Nimbus' mouth shut.
  • Paranoia Fuel: The Monster in Freeport Venture: The Hunted, who can show up anywhere, and prefers to hunt in the dark where you can’t see it. The best example is in the second chapter, where it gets into a supposedly safe room, with no windows and a guarded door, and carves an extremely accurate image on the wall of Kukri sleeping. Which must have taken it hours. While she and her parents were asleep in the same room.
  • What an Idiot: As a filly, Rainbow Dash is incredibly bullheaded, to the point where she seems actively opposed to having an actual plan for anything. In the present day, she's only gotten a little better, with most of her plans boiling down to "Throw myself into the thick of things with no forethought, then make the impossible happen." The fact that she's still alive, let alone still has a job, is a testament to her skill and raw charisma as a leader.
    Derpy: “Rainbow, you idiot. You jumped into a cloud without checking for lightning. Again.
    • After an argument where Cloud Kicker calls Derpy too possessive when she expresses concern that Cloud might leaver her for Fluttershy, she kicks Derpy out because Fluttershy overheard it and cries, thinking she's driving a wedge in between them. Then Cloud Kicker gives into her impulses and has sex with Fluttershy, and afterwards desires to marry Fluttershy before anyone could object. It's hard to be too concerned when your marefriend does this once you leave.