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I'm a huge fan of Monotypes, but those are the only type of challenge that I've done with any frequency. I don't really like Nuzlocke challenges though.
@Joe: Wedlockes are pretty hard, since you have your team made up of three pairs of one male and one female Pokemon and you can only switch between the two Pokemon in the active pair during battle unless both die.
Watch Marriland's Heart Gold Wedlocke series and you'll see what I mean.
It was Marriland's wedlocke series that actually influenced me to try it out. I'm enjoying it so far, but I've already ran into trouble with only being limited to switching between two low levelled pokemon.