Roll-a-boards are the devil IMO but then I'm not usually dressing up when traveling. I tend to use a probably somewhat larger 40L Osprey than what you use but i

Roll-a-boards are the devil IMO but then I'm not usually dressing up when traveling. I tend to use a probably somewhat larger 40L Osprey than what you use but it's a lot more flexible than the standard carry-ons to put in overhead.