I think Roland is damned as soon as he let's Jake fall. When the Tower finally falls he'll see that he has been living inside a blade of grass on an alien world.
Saved: the next loop is the last before final salvation
Saved: after a number of loops
Saved (neither of the above: give your own version)
Damned: the next loop is the last before final damnation
Damned: stuck in the eternal loop forever
Damned (neither of the above: give your own version)
I think Roland is damned as soon as he let's Jake fall. When the Tower finally falls he'll see that he has been living inside a blade of grass on an alien world.