Join Date: May 2006
Location: MYF/CMA/SAN
Programs: COdbaUA MM, AA EXP, AF G, Bonbon Gold, Hilton G, All G, GHA Titanium, Hertz PC, Avis Presidential
Posts: 5,929
You clearly can't rely on a one bag solution because of your 2 laptop dilemma. I don't even do one bag - the lowest I go is an Air Boss/Gator combination that I use for traveling in Europe when LH might be involved. Otherwise, I go Sky Train or Air Boss plus CPA Briefcase.
I do think the idea of having a rolling briefcase with the Air Boss is a nice combo. The Claw strap could be modified quickly to attach to the roller.