I'm looking for a smaller carry-on bag for frequent plane travel. I've been using an Aeronaut-Synapse combo for recent trips, but I am curious about being able to trade the Synapse for a Ristretto for iPad, Small Cafe Bag, or Co-Pilot.
Ideally, I would want to easily fit an iPad and Bose headphone case in the bag, with room to spare. But I think those two items are the largest/bulkiest in the mix.
A padded section for the iPad is not mandatory for me; I have a very slim padded sleeve already that I currently just throw in the Synapse. It's about the thickness of the TB Padded Organizer Pouch and works just fine.
Room for an insulated Kleen Kanteen (16oz) would also be killer.