The Espada win both scenarios
The Espada win scenario #1, but not scenario #2
Soul Society win both scenarios
The clones aren't proof of her speed. So then, what evidence suggests that she's faster than all of them? Surely not just because she's Captain of the stealth corps, right?
In my book, Soi Fon doesn't have the ability to blitz Ichigo so badly twice that he'd lose resolve immediately and doesn't even attempt to pursue her, even if she was purposefully handicapped (base Stark) and carrying Orihime to return to Aizen (Ichigo just nearly died to save Orihime). So in my book, Stark is faster than Soi Fon.
It actually does mean that. Think about it; Hachi was able to put up an incantation before Respira caught up to him, and then was able to cast another incantation to teleport his hand into Barragan's body immediately before Respira traveled from his hand to any further point in his body.
At that point, Respira was from a bloodlusted Barragan. It's doubtful that there's no Captain that can complete an attack before Hachi can't complete a Kido
You're right. I mean in Soul Society Chad was secretly planning to be more evil than Aizen, until Shunsui stopped him, right? And Ukitake was on his way to usurping Gin until he was beaten by Lillynette. And the less said about the Vaizards, the better...
Good guys don't always win. Ichigo always wins, if he needs to. That's it.