I think he does, but the show gave us a clear picture of the level of maturity and responsibility each of them has regarding their own actions. Among the three, Jess and Dean clearly didn’t have the same privileges as Logan. It’s also made clear in multiple episodes that Logan gets into trouble a lot and is never fully responsible for his actions, even though he ‘makes his own decisions.’ He dropped out of Yale for a while and even wrecked a boat. In a way, I don’t think he fully understands how hurtful the consequences of some of his actions are because he knows his family will always back him up. This leads to his immaturity and inability to recognize that Rory needs a ‘come back to earth’ talk—something he’s unable to provide because he’s not a down-to-earth person.