I have a rather unusual requirement.
I have to carry my laptop, customer laptop, two iPads, chargers and such, and books for MBA classes. Due to data security this bag MUST stay in the cabin with me, regardless of cabin size (RJ) etc. On the road about 20 weeks a year.

I have been using a 20" roller for clothes and a bag for computers. I realized I am carrying the heavy stuff and rolling the light stuff.

Considering a Travelpro Crew 7 for computer stuff:
http://www.overstock.com/Luggage-Bag...0/product.html

I need to put the clothes in a bag that can go on the handle of the computer bag, and has compression straps (and can be gate checked if required). I like the Airboss and SkyTrain, but they won't nest on the handle of the trolley.

Any suggestion for the clothes bag, or better ideas for the trolley?