Get a difficult task, Get a terrible Reward

[Master Chipper]

Reward: You're stuck in that district forever and can't teleport out

Task: Solo 10 C.E.O.s without taking any damage. If you take damage you have to start all over

[Happy The CCGer]

Reward : nothing
Beat Shockley at coding

[RIPToontown365]

Reward: He hacks you for life in anger.

Task: Get a level 51 Cog Disguise of any kind.

[Happy The CCGer]

Reward - 1 pie
Task beat gangster Joey in a rap battle

[RIPToontown365]

Reward: Get fired out of a cannon and become a slave for the cogs forever.

Task: Throw a wrench in the TTR Dev's system.