Your roleplays will be judged on 5 pieces of criteria, and if you are ahead of your opponent in this criteria then you will win your match.
1) Creativity - There was a few people that had a problem with the way roleplays were rated last time because they felt that holding a mic and hyping the match or whatever was repetitive and it was hard to be original. Well now you are completely free in what you write and have no restrictions, so originality will be rewarded.
2) Hype - Originality will be rewarded, but this is still a wrestling promotion. Your rp's must still hype the feuds your character is in and the upcoming match he is involved in. So keep that in mind when you are trying to come up with original concepts.
3) Character Development - How your character changes and grows in your roleplays. Specifically character development relevant to and within the feud, because development for the sake of development prolly won't help you win the match, cause its pointless. You must also show whether you are a heel or a face in your roleplays, and also if there's any background information you'd like to give on your character, this is where you do it.
4) Writing - Your writing skill, which includes structure of the roleplay, grammar, spelling, dialogue etc. How well you write the roleplay basically.
5) Realism - Basically how likely or true your roleplay is...so if you're out stargazing one night when suddenly you're abducted by aliens or something, you prolly wont score high in this area. Unless you do the "and it was all a dream..." ending, but then that'd just be lame.