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Hmm... Not sure how flexable the system is,
but once you get a HM you could make one where you have to give someone a pokemon that has learned the HM.
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Mission: Sam's Razor
Description: I accidently lost my HM cut, can someone trade me a pokemon that has learned cut? -Sam
Reward:
Need: A Pokemon that has Cut
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Mission: Stranded
Description: Help, I'm stuck on this island. Please trade me a pokemon that has HM Surf - Samantha
Reward: ???
Need: A pokemon that has Surf
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