I currently use the Ciao bag and a nicer Eagle Creek ES2 Round About before that for trips up to 3 nights. I slide a very small Amazon Basics 11.6" Laptop Brief on top to carry my Surface Pro, notebook, and chargers/gadgets. I fly in jeans but wear my sport coat or suit jacket so I don't have to fold/pack it. Along with Eagle Creek Pack-It Folder 15 for dress shirts, Pack-It Cube for underwear/socks/undershirts, and pants folded on the bottom I have no problem doing 3 nights (though some re-folding of dirty clothers is required to keep it from bulging on 3-night trips).

I like being able to put the Ciao bag up in the bin and have my small brief under the seat for easy access. I can also put the Ciao underseat if necesarry and find a small crevice overhead for the small brief (haven't had to yet). I've also never had to gate-check the Ciao and it's easy to close the handle and hand-carry both if I see a gate agent or gate-check agent who's pink-tag happy making everything rolling get checked. Even on Q400s, I haven't had to gate-check yet.

I probably wouln't buy the Ciao bag again as after only 4 trips it's already dented the handle slide channel causing it to hang on extenstion/retraction. I'll probably be getting another Eagle Creek ES2 even though it's not as crazy cheap as it was a few months back. If don't mind spending the money (it doesn't look like you mind) then go for the U116 or one of the other similar B&R bags.