Oh are you a Sam fan? In all honesty I forget if Dean did that. But Sam mostly got back into hunting for revenge on Jess. Dean had only begged him to help with their dad in finding him.
Don't really remember Skin to be honest. I like the actor of John, but I do not like him as a father. It seems he can only be a good father with Mary around. Too much neglect in my opinion to truly like him, but that's just me.
I honestly preferred Bobby as the boys father figure, since he spent time with him and tried to get them to do normal things. But again my opinion on that matter though.

But yeah some things does bug in certain episodes and seasons, so I get where your coming from.