For the past few weeks I've been making 2-5 day trips using my Imago, Western Flyer, and side Effect. The Imago carries my iPad, 13" MacBook Air (in its Cache), folders in a large organizer pouch, and various chargers, etc. in organizer pouches. The Western Flyer has my clothing, toiletries in a 3-D Organizer Cube, and my Swift (for carrying things around when I don't want the computer, which stays in the Imago). And the Side Effect is for the essentials in a small package.
The picture shows the bags while I'm waiting at the gate for my flight. Usually the Western Flyer isn't packed to the gills, so I stuff the Side Effect in the zipped up rollerboard pocket to consolidate bags when the the gate agent is being strict about 2 carry-ons. Once on board, I can take it out and put it under my seat with the Imago without holding up the line.