Well, I like Logan so I don't think there is anything wrong with Chris liking Logan. I don't think Logan is arrogant and self-important, he's just too used to getting his own way, and he's a bit hot-tempered and impulsive. But I think he means well and just has some growing up to do.
As for Chris, I can see him getting into trouble. Not out of deliberate rebellion, but from a lack of direction or purpose to his life.
But I agree Chris was a better-developed character in Seasons 1 and 2. In Seasons 5 and 6 he was just an obstacle to Luke and Lorelai, someone to drag Lorelai back to her (supposedly) immature and unhealthy past. In Season 7 I don't think the writers did Chris' character justice at all, considering his amount of screentime. We had much better Chris-Rory scenes and learned more about Chris' life outside of Lorelai in Seasons 1 and 2. In Season 7 Chris' presence was
only about Lorelai and the writers just had Chris behave in whatever way they needed to further their Chris-Lorelai romance plot.
I think David Sutcliffe gave Chris more depth than he could have had and still made me love Chris, but frankly, they could have done a lot more with his character than have him trailing Lorelai through the streets of Stars Hollow like a lovesick puppy dog, demanding houses, babies and new Christmas stockings ASAP, or ranting about a stupid plot device (aka custody letter).
By the way, although most people don't seem to see it which makes me feel odd for mentioning it, one of the reasons I like Chris-Lorelai interactions (romantic or otherwise) is that, especially when they're happy and having fun around each other, the interactions look
real. I sense that a little bit with Rory-Lorelai and Rory-Chris too, but not at all with Luke-Lorelai. Their interactions may be good, convincing acting--but it's still
acting, and maybe I look too far beneath the surface of the characters, but I've somehow always seen obvious differences in the types of acting. There were moments (mainly in the early part of the season when Chris and Lorelai were happiest together) when to me it looked like LG and DS weren't really bothering to get into the Chris/Lorelai characters, they were just enjoying being together and simply letting their real feelings show up onscreen. I've heard they are good friends and honestly I don't see how I could believe otherwise. Even the best acting can't match the way two people interact when they really know and like each other, and that's just the sense I get with those two. And it's enjoyable to watch.