Thanks everyone, this is really helpful (especially the travel ninja thread).

I do have a great Briggs & Riley 15.4" expandable briefcase. I pub my laptop in there along with toiletries, cables, chargers, etc.

Question: what do you all recommend for packing dress shirts? I've never been able to keep them from wrinkling in the folding compartment. The last few trips I've asked my local cleaners to fold and box them, and I just put the box directly into the carry-on. But that's for overnight or two night trips, and it's not space efficient so it won't work for this.