The Rebel Faction

Although you do bring up good points, it may be I left a few assumptions in my original suggestion. Basically, I wanted the jedi to manipulate these answers into being, not suggest openly - much like as a strategist moves pieces on a board, so too would Regrad be used. Regrad follows the will of his Gods, and his Gods are connected to the Force, so if the Jedi had this plan then perhaps they could use that connection to manipulate Regrad into following the surrender without him even knowing from where the idea truly came. The military would feel betrayed, but would not know the one who originally brought up the idea for them to flee to the Onyxian commonwealth was in fact a Jedi and not one of them. That sort of subtle manipulation.

That way, when Regrad proposes surrender, some people follow his order in hopes it's some sort of plan, wheras the military leave - no one knowing it was the Jedi's plan for this to happen. As the plot currently stands, it appears that Regrad is the one who defeats Simon by surrendering and then regrouping to fight back with the truth and a returning fleet. I would think Simon would have accounted for any strategy Regrad could have come up with, since as you said, he is a known quality - what he couldn't predict would be the machinations of the Force, and it's agents, who instead give the various lightsiders their answer through manipulation. It would also help in the 'Fall' part of Simon's life, as he would be struggling against fate itself.

However, over the ten years between now and the rest of the story, not only does that commitment die but the Jedi itself seem to break up.

I'm not quite comfortable with the idea of the Jedi fading away again when we are so close to actually becoming something other than "Yes, we're the Jedi Order. There only about five of us, of course."
And your manipulation ideas seem to come pretty close to the Dark Side... if we were something like the Empire or Shadow Jedi wossnames, it wouldn't be quite so bad. But we are the Jedi Order. Under lightside factions. Normally we don't run around manipulating people for our own schemes and sit in dark rooms around a table and using secret handshakes.

He became a Jedi master because of it, too.

Nah, I guess they're right. It doesn't sound too much like what the lightside would do - to be honest, that's why I thought it would be a good idea, catch people off guard with it. Also, the Jedi just didn't seem all that important in the story, basically just cannon fodder for battles they choose to be in and maybe one important mission. This way, I thought the Force and the Jedi would have a more leading role, since right now the story could probably go on fine without them, and that didn't seem Star Warsy. On the other hand, neither would be having them as chief manipulator strategist guys. It should probably be fine as it is then.

*Trys hand shake but accidentally gets tongue tangled in hands*