I know the Tumi is a slim version but if you look at the picture it appears to me at least pretty thick to carry in the Air Boss. The OP is spending some serious money on the stuff he has asked advise on and in my opinion he will be carrying both bags after he packs the Air Boss with all the stuff he is mentioning.

Myself I love packing folders and cubes but that is me. I also like clothing that travels well that doesn't require a lot of maintenance. If you have such clothing already fine but if you don't take a look at Travel Smith, Tilley, ExOfficio, and others make clothing that travels well.

While it is much easier to wear shoes that you can take off easily they are not the best choice for me. I wear the heaviest bulkiest pair and pack the loafers leaving more room for clothing.

Shak