I love the look of your luggage and would be interested, with a couple of concerns. As one more road warrior who usually works with C-suite at clients (plus some very wealthy business owners), I could use a more elegant looking luggage. Function matters to me more than form. I am using a Kirkland spinner (
http://www.costco.com/Kirkland-Signa...100080005.html) rather than my Tumi International two-wheel carry-on. Both can fit a suit (but both rumple suits). Because I usually fly business or first, I have now taken to just never putting the garment sleeve from the bag inside the bag and hanging it as soon as I get it on the plane. But, there is always a danger I will forget.
To take care of a week back, I strongly prefer 4 wheels to 2 wheels.
To keep things light, I use a painfully class-free bag from CaseLogic that cost me $23 (
http://www.amazon.com/gp/product/B00...?ie=UTF8&psc=1). Your briefcase looks good, though I am not sure I would be able to stuff in the various electronic items I take with me (Apple powerbrick; international power adapter, travel extension cord, charger and cables for ipad and phone, emergency battery power for phone, plus glasses, business cards, ibuprofen, etc.). I also have a shoulder strap that I love -- really spreads the weight out well (
http://www.bhphotovideo.com/c/produc...rap_Black.html). I doubt that your clever leather strap solution works as well. Are there hooks to attach an external strap to?