I always set the top of my pants slightly below the top edge of my boxers, so you can see the top of those if I lift my shirt up, but it's not like my ass is ever hanging out.
No. Whenever I wear jeans, I always wear a belt to insure that my pants do not sag at all. I'm paranoid about it. I don't understand why guys do that anyway. How is having your underwear showing "hood"?? It's stupid as hell.
The top of my pants are always set slightly below the edge of my boxers and right there at the cup of my buttocks you can see them if I stretch or lift up my shirt but that's as far as it goes.