I've most recently sworn off checking luggage for trips less than a month; my rollaboard is one of these (on the left):
Unfortunately it's no longer available. Downsides are that it doesn't fit wheels-first in to older style B737 overhead bins -- and the design means there's some wasted space .. upsides are that it's incredibly well made and easy to lug around.
My cabin bag/tote thingy is one of these:
Fits everything I need for an overnight trip, plus it looks awesome
Unfortunately it's no longer available. Downsides are that it doesn't fit wheels-first in to older style B737 overhead bins -- and the design means there's some wasted space .. upsides are that it's incredibly well made and easy to lug around.
My cabin bag/tote thingy is one of these:
Fits everything I need for an overnight trip, plus it looks awesome