I must have been in some kind of mood tonight. I went ahead and typed up a whole plan (with questions) for the entire game. Suggestions for more questions are still welcome at any time, of course, but I just felt the itch and had to scratch it.
I've also sent a copy to Lex in case I become unable to continue leading at some point in the process, so we have a backup plan. [EDIT: I see our PM system sucks at maintaining the board's own bullet list formatting; sorry for the mess, dude.]
By the way, I ended up deciding on just ten chapters for the whole thing. That's two and a half months. I decided on this for a few reasons: 1) I think people will start losing interest after any longer than that, and that if the playthrough doesn't maintain momentum, we'll see the same thing happen here that happened with some folks in the last one; 2) FFVIII really isn't that long and doesn't require much leveling at all; 3) Lightning Returns will be coming out around the world in February; 4) the FFX|X-2 HD Remaster may be coming out by then too, so peeps will want to have this playthrough finished.