Brainstorming: I've already proposed Korri assemble a team of gymnasts.
Second idea: I propose Ren "taking over" the photo/gravure story, as you and her pursue models and gain followers.
Finally, I propose the player team with Tassy on a two part history project. The first half would be a paper due on day 50. The second half, a presentation. Their subject? The Honno-ji incident. This is something SimMan himself came up with.
http://www.freedomwall.info/post/5550672/honn-ji

As the player digs deeper into the history of Oda Nobunaga, various flashbacks give the game a historical perspective. A 16th century SimGirls, if you will. The dateable characters need to step up, as Ami and Karin took a lot of side story with them.