Can you see him going up to HW?
Unless Cain retires, I just can't see him doing it. I get the feeling they're pretty good friends, and wouldn't want to crush one anothers dreams if they were to fight each other.
Legacy wise, you make a good point. There's always going to be that thought in majority of peoples heads that he was given the title. But as we know, we had a champion that was cheating, so DC is the real champ. I hope DC realizes this, and doesn't feel the need to prove himself at HW.
I would like to see DC challenge himself at HW, but another part of me would like him to finish his career at LHW and continue cashing that championship money.