If you rotate your mast so it points into the wind, it should not be a problem unless it hooks shrouds or trapeze wires while raising. But pointing the bows into the wind really is the preferred method.

There are two schools (I think) on sail rolling. Those who rolls from the foot and upwards to speed hoisting next sail. Then there are those who roll from the top and down, becouse they think this will be kinder on the sail.