Frequent flyer for more than 10 years. I've went from no clue, to rolling everything, to throwing everything in the bag at the last minute. I range from 60 flights to 140 flights per year, and now I simply hate packing until I have to.
The one thing I do is find clothes that are less prone to wrinkling, and are iron friendly. Second is waiting until the last minute to pack, and hanging everything in the hotel the minute I arrive.