I get upgraded lots and and am preferred with most airlines, so I always carry-on and never check (I'm at an airport now).
If you're lugging weight, wheels are best and backpacks second best. Tumi is the way to go for either.
If you pack light and don't have to haul a laptop, the op's bag looks killer. I'd do it.
And guys, don't look like an amateur when you travel. Pjs, sweats, cloth bags, Nike bags, flip flops, winter coats, scarves, shorts and smelly sandwiches, et al mark you for the fool you are and you'll be treated accordingly.
And lose some weight, for Christ sake, if you're in a middle seat.
And blow your fucking nose!! I don't wanna listen to you sniff for 5 hours.
Oh, and Bose noise canceling headphones are wonderful.
Living the fullest life means leaving a history of goodness behind you for others to remember.
Cherish the memories------Ken OBSC