I have used my Airboss twice. The first time, it was downright painful. The second time, it was uncomfortable. The problem with the Airboss is that you can really overpack it. When heavy, the claw strap HURTS. If I keep it to a medium weight, the claw strap is uncomfortable. I have bought a Tom Bihn Absolute Strap (half price at Amazon) but haven't tried traveling with the Airboss with the new strap.

As a comparison, I have recently bought a Tom Bihn Aeronaut for family travel. Having two small kids, having a carry on backpack frees up my hand to hang on to them. The Aeronaut is significantly more comfortable than a claw-strapped Airboss. I would definitely choose the Aeronaut for future travels without hesitation, while the Airboss, to me, is the bag of last resort.

If I were to do it over again, I would buy a Tom Bihn Tri-Star instead of an Airboss. Having the option of using it as a backpack is a nice luxury worth paying extra for.

I still prefer a roll aboard instead of the Airboss. Frankly, I am still traumatized from the pain caused by the claw strap. Choosing between a roll aboard vs my Aeronaut is more difficult. That would depend on each particular travel situation.