Speaking of WF cubes and organizers, I had plans to buy an Eagle Creek Pack-It 15 folder for my Synapse 25. The Pack-It folder will also fit in the WF. In your opinion, would a regular large WF packing cube be of more importance than the Pack-It folder for organization?
It really depends on what you are packing. I've found that when I'm taking dress shirts, the sleeve can be helpful. For most other things I prefer the cube since it maximizes the bag's interior space. The sleeve does compress things a little bit, but you don't want to mash the daylights out of it since doing so can cause creases in your clothes.
I have a silly question about the Western Flyer, if you don't mind...
If used in backpack mode, does the WF offer padding of any kind against the carrier's back? I'm just wondering how comfortable it is if you're lugging your luggage around an airport, train station or bus station.
I find my WF to be comfortable and I usually only carry it in backpack mode. I shlepped my fully loaded Aeronaut through multiple airports as well as through Berlin for 6+ hours and never felt uncomfortable.
There is not any padding but I find it conforms to the body (i dont carry a computer in the back section). The chest and waist straps help with this. Not a silly question btw.
I've found the WF to be comfortable in backpack mode - example was using it recently for a weeks holiday in the Canaries, so the clothes in the rear section nearest my back acted as padding. I put the shoes in ones of the front two sections so they couldn't dig in. Backpack straps were a godsend for changing trains in London and then when we got to the airport. Hands are left free, its not too big so you don't take anyone out when turning around, or get caught up when going through ticket barriers.
I've used it a lot for short trips/overnights for work when my laptop and work gear go in the rear, but I tend to use the absolute strap for those trips. If I was using the back pack straps I'd make sure my laptop (in a neoprene sleeve) would end up at the bottom when in backpack mode, and the 3D organiser cube with the chargers etc would go at the 'top'. I've usually got some documents in a large organiser pouch, and putting those right at the back might help minimise any discomfort. Hmm, I feel a practice pack coming on sometime soon!