I struggled at first. Kept them very simple and still kept screwing up. Eventually I realized to make the story in the database outside of the saved game. That way I could modify it and fix the screwups. Still, its a bit of an involved setup. I've done a couple and I found the easiest way was to outline it on paper and then work on creating it. Plus, once you lay out the matches and big plot points you can easily go in and add interviews or attacks or extra matches how you want them. Or, I did a 3 way feud story and then I was able to copy the story and make a 4-way feud by building off that and adding the 4th guy without having to start from scratch. I'm nearing the end of my game's year so when I do I'm going to take some time and try to create another couple of stories. I'm still not good enough at it to make the story I want when I want it, but trial and error.
For what its worth I've found the Catalyst, Support, etc stuff doesn't hugely matter. I tend to make all the relevant players in my stories Catalysts just so I can evolve them if I wish. Otherwise its just a matter of knowing which slot every fits in so it helps to have a person in mind or to at least label them "Heel", "Face", "Heel Lackey", whatever. Again, just give yourself a piece of paper to reference. "Person 1 = Main Heel; Person 2 = Main Face; Person 3 = Heel Manager; etc). Then its more about giving them the proper thing to be rated on and the individual angle "catalyst/support/target" stuff can be double checked by seeing what angles fit.
Slow and deliberate would be my suggestion, I guess. Do something simple and do it in the database so you can edit. Then when you know that works, build off it. If you just try to do a crazy 8 person story with divas and managers and authorities right off the bat you're probably bound to screw up. Trust me, I made the same mistake.