I didn't know you wanted to check the bag. I was suggesting doing something like the AirBoss for clothes and toiletries (Al and Jim have used it for 2 weeks worth of clothing I believe - see previous posts) and a *smaller* laptop bag for stuff like papers/laptop, stuff you may need for business (like Tom Bihn ID or maybe something smaller). I have carried an Aeronaut (with two packing cubes in the middle section) + Tom Bihn ID successfully for week long trips with no problem. Of course, I am slightly smaller than you so my clothes may take up less space. I think it really depends what you plan on taking. The reason I suggested the Air Boss is that I think it might be better if you are packing things like suit jackets. It can also probably hold more than the Aeronaut since Cordura seems to expand more whereas the Aeronaut really keeps its shape.
I cannot really help out with wheeled suggestions since all the wheelies I have are pretty crappy and cheap.