I haven't actually come up with anything more on Theorycraft #4, but I thought I'd share my musings in case they spark somebody else to the answer.

The obvious interpretation of that line would be that Ciro dies at the end of the cycle, then everyone gets reincarnated and the cycle starts over. Except, it's unlikely that Ciro just needs to die; heck, we've already done that. The "defeat" must be a specific thing, and probably needs to happen in a certain way for the desired consequences to take effect. The half-formed idea I've been toying with is, what if Ciro's death isn't actually the end of the cycle, just the end of his/her role? It could be that the defeat is simply required for the important part of the cycle to happen. What that might be, I don't know, hence why this is just useless ramblings and not a proper theory! Probably impetus to make another character act, or maybe we'll give narrative control to someone in the final moment. Maybe the whole thing is an elaborate plot to get Ciro to give Oric narrative control via the Astral Influx?
The bit about Oric's plot makes sense.
As for what constitutes defeat...hm. Maybe cycles end either when Oric is (permanently) killed or Ciro is captured(/permanently killed)?
She could have a brother? Or a whole family?
Who says she doesn't? :3
Inb4 "You killed my family in the arena, prepare to die."
So all Goombas are related? You racist! They're mushrooms, not hillbillies!
Goom-Bess is even a different color, although I'm willing to put that down to gender dimorphism due to not having studied Goomba physiology.
Anyways, I didn't know Cherish was a healer. I would not have suggested killing her if I knew that. I'm starting to think I missed an update.
Or possibly the entire bit when we met her the first time.
And the healing spells in her inventory.
And, again, why would it be a good idea to begin with? "You killed my friends? I WILL KILL ANOTHER OF MY FRIENDS NOW."
However, theorycrafting isn't the only problem - arguing about suggestions has the same cluttering effect. What would be really nice is some way to view only updates, hiding all of the intervening posts.
Well...hm. Two possibilities. 1: Someone indexes all the turns, like I do with A Beginner's Guide, and the index is linked from the OP. 2: Someone figures out how to only view freeform's posts.
Oh, and welcome, Scionox. I'm the most consistently sane Bay12er. Glad to meet you!