I can throw you an event after you have your character go outside. Odd and Ulrich actually aren't the types to write a diary. Both Yumi and Jeremy have actually mentioned that they wrote diaries, specifically in the show. Odd, he hates studying, and doing things out of his way. Why would he waste time writing about the past, when he can be doing something in the present!? Ulrich wouldn't either, since he would be busy trying to catch up on his grades so he wouldn't fall behind. Plus, he usually goes and trains himself to let out his emotions.
I do have something planned about Kiwi though, but I'm not exactly sure how it would work. I already know Odd's sister would have come to get Kiwi, though I'm not sure whether to have Odd get in trouble for Kiwi being discovered. Maybe since all the rooms were messy, Jim didn't even discover the dog, and Odd's sister saved Kiwi at the last second, and still managed to make sure he didn't get caught. I plan on our character's actions with this, to go to Odd's house, and some interaction with Kiwi. I'm not sure exactly yet, but I think it's going to end up be dog sitting, and Kiwi goes nuts or something. xD
As for getting you into it... maybe not yet. After the first return to the past, there's going to be a big thing happening. I'm sure both you and Gamer know what I mean, who comes back, and that should bring interaction. Plus, the other guys show up around the same time, so that's more interaction as well. Oh, and please don't say who's coming back, or who the other guys are. I'd like to keep them a secret to the newbies here. ;).