Sorry to be a pain , but at what point should I start thinking about these?

I am basically at the point at the moment , of being reasonably happy with the way I follow progressions on open chords , but kind of sucking at following a tempo on barre chord progessions .

I suppose my first major goal as a guitarist is to be able to play something along the lines of either , the hollies " long cool woman in a black dress " or jimmy eat worlds " the middle " both involving good rythym and good muting .

I suppose I could answer my own question with a " once u feel comfortable with x , move onto y " type thing , but does one ever feel truly comfortable? thoughts and answers appreciated pls=)