Over 22 years, for the "small personal item" I've been through an old school chart case, two or three backpacks, and one or two other bags. At present, I'm using a Blackhawk Range Bag. All have had pros and cons but this one fits under an airline seat better than most. Nothing is perfect.
As for rollaboard, an old school 26" Purdy Neat lasted more than a decade until the frame bent. Wicked heavy but rugged. Now using a Strongbags 24". Lighter but not as much capacity. Fits in ALMOST every mainline overhead which is good since I only check a bag when the airline holds the proverbial gun to my head.
Find yourself the lightest bag possible and really edit the clothes you drag around on the road. You'll have less layover time than you think. Pack accordingly.
Good luck and welcome to the minstrel show.