Thanks, 1k+!
There are certainly other valid packing techniques and it depends on what kind of things you take exactly. But this method has worked fine for me for what I think is a pretty generic packing list.
I should add that the outside compartments of the roller would receive three things:
1. The 311 toiletry baggy.
2. The in-flight bag, containing eye mask, ear plugs, ipod, pen and other necessities which you know you need in-flight. This way you don't have to get up to search them in your bag.
3. A little bag with the stuff you need to take off at security like watch, wallet, keys, chump change. All that goes in the bag even before I step into the security line. This helps a lot.
Till