First, a quick typo, in the block “Who Are You?” you have written “posess” instead of possess (missing the first double s) note - I don’t knock points for typos haha
Okay that out of the way, I enjoyed reading Lookback and I think there is a lot to like about the general vibe and ideas there in. I do think it would take a bit extra prep for a warden to get the most out of this in its current state but I think you are close to something super cool.
One thing to think about is how Agent X has become swept up in the “Game” of it all and is hostile to the characters… what if instead of one agent there were two, and they have both become integrated into the game, each on a different side of the war, not only do you need to find them but you have to bring their sanity back to them… The PCs could try to join one faction and help them “Win” so the game will be over, or they could learn about the factions and have to “Talk Down” the Agents, or learn about the agents and bring them back to themselves… there are a lot of cool ways i think you could use the pieces you have to make a cooler end result.
Regardless, I had fun reading this one and hope you do a post Jam version from the notes you are getting because this is an idea that deserves you going the extra mile to bring it to its full potential!