Jack isn't ever going to ascend. Hussie can afford to let Jack dwell in Complete Monster territory the rest of the adventure without losing dramatic opportunity - he does have a morally-dark-grey counterpart in Spades Slick. e- whoops, misread last post as 'Jack' not 'Jade'.
I find the core story very interesting as a whole (to-date) right now. The players are given a very interesting and unique (not to mention cryptic) game to play, that you only learn more about as you play. However, through interaction with the trolls we begin to see that this particular session isn't going to be played normally (and in fact cannot be). The players have virtually unlimited power, or the means to create said power, so long as they're smart enough, even to break the game's boundaries. So we get an interesting "the game can't be beaten traditionally" story while still discovering through all the side info we know how Sburb is supposed to play.
It reminds me of Portal. If it was just 'a computer with a really dark sense of humour guides you through a death course' it'd be pretty cool, mostly because of the mechanics. But you get to see the Rat Man holes, and begin to think about what kind of a facility would make such a test in the first place, and why this computer is so messed up, and how you ended up there, and all this other stuff that may never have crossed your mind. Rose's last GameFAQs message gives me the same "fuck yeah time to break the rules" vibe that breaking out of the facility and hunting down GLaDOS did.