You won't be able to properly pack a laptop bag INSIDE the AirBoss - I tried, and failed miserably. The solution was to get a nice ballistic sleeve for my laptop, so I could carry it around while on the ground.

One of the drawbacks of the combinations you are looking at, is the weight of the entire setup, once you are packed - eventually you may get tired - I did

I can vouch for the AirBoss in terms of quality - it is a very well made bag - was sad to sell it, but it just didn't work for me - went to another product.