Excellent work in making a timeskip tool that's simple to use but quite compelling. Perfectly hits the theme, and the way the contents are laid out is fantastic.
The one critique I have regards the Take on an Apprentice activity. I believe it doesn't fully account for retainer advancement rules, given the examples in the Monsters book describe how retainers immediately shoot up to their mentor's level when recruited if they're not higher already. Worth considering how that interacts with your rules for their level equaling the seasons spent training them.
As an aside, it's been very funny watching other submissions (including my own) bounce around the #2-5 popularity spots the past few days while this firmly holds #1. The community has a clear favorite to win this thing. It's well deserved.