At this point any more apologies are probably going to sound empty, but I can't update this quest as it is.
@veekie hit the nail on the head, there's just way too much micro and I've already set myself up for failure. This next update would have required almost 70 rolls, and there are currently 24 different things that can be trained. If I do start this quest again, it'll be using a system that requires far less micromanagement than this. I never intended to write something as involved as a CKII or AGG style quest, but ended up getting lost in the numbers anyways.
If I do restart this quest, it'll be using mechanics that are far more simplified, but until I can figure that out this quest is going to be dead.