I am considering the Air Boss subject to how my travel changes over the next year. My main concern is having to carry it through the airports - although with my rollaboard I think I am getting "tennis" elbow from dragging it around...
Also considering a Tumi sports duffel...
I got the Air Boss about 5 months ago and have done 24 flights since, a mixture of domestic and international, and find it great, used use a Samsonite rollaboard, and can now fit the same amount of stuff in and be over 1KG lighter. I find it is easier to pack and find things and also work shirts can be folded and remain almost wrinkle free. The shoulder strap is great and makes it easy to carry even over longer distances. And if flying on Dash-8s it goes as carry on, rather then my previous bag was nearly always required to be checked.
I also got the Metro Briefcase at the same time and use it daily for work carrying my laptop. They are both well made and very easy to use and carry.