I generally run an old Wenger "Swiss Army" Carry on size, 2-wheeled bag (rollerblade wheels). I think I paid $45 at TJ Maxx. I've had it for nearly a decade... all over North America, Europe, South America, Central America.
I've joked about trying to kill it to buy another bag. I've wheeled it aggressively down staircases... packed it overfull (even with the zippable-expansion)... slung it around by the extended handle while full.... It's light but somehow it's bombproof. I've had to take hair trimmers to clean up frayed edges and wash it by hand... but it's essentially in like-new condition, functionally.
I use an
Osprey Porter 46 backpack for situations where I want a carry-on sized backpack... ie: lot of walking/travel between stops on surfaces where roller bags suck. If I'm going to warm weather for a week or two... or colder weather for a week. This is my bag.
On longer trips I combine the two. I could pack for 6 months in the Osprey/Wenger.
My thoughts on bags:
1) Wheels: I like two wheeled bags, preferably with replaceable rollerblade style wheels. 4 wheel spinner style rollers SUCK on any uneven surface. They roll like less efficiently when tilted. Unless 90% of your wheeling is done on perfectly smooth airport floors, you're better off with a quality 2 wheel bag.
One selling point for spinner bags is they stand on their own... but good 2 wheel bags do too. Spinner style wheels tend to be more prone to damage and/or getting hung up on stuff.
2) Internal Space: I dislike bags with ####loads of segmentation of internal compartments. At that point I'm having to adapt my packing to fit the bag's design. If you're always going to the same place and packing the same things... and those internal shelves and such work for you... Great. Me... Let me use Packing cubes to customize the internals of my bag to my needs. Give me a blank slate to work with.
3) Packing Cubes: Yes. So much yes. You can access items without having to be cautious to not have to fully repack the bag anytime you need something. YOu can compress items. You can organize (shirts in one cube, pants in another, underwear/socks in another). Mid trip you can break out dirty/clean clothes. You can easily transfer cubes to dressers without fully unpacking, etc. Nominal added weight and volume, but way more flexibility.
Regarding brands... Have heard good things about Away. If I didn't ####### love my suitcase so much, I'd jump on this promo as a Chase Sapphire Reserve cardholder. I agree with shunning other more expensive brands in favor of Away. Not due to personal experience... but due to reputation.