Normally I will spend far more than necessary on things just to get good quality, but I've never made the plunge into Expensive Rollaboard Land.
I have an American Tourister that I picked up at Staples/Office Depot for $69. I've had it for 2-1/2 years now, slightly more actually. This bag has led a very hard life... It goes off and on the plane practically every leg, so the rampies have probably had their hands on it around 1500 times, not to mention the number of times it's been beaten, dropped, been at the bottom of a full cargo bin, and abused by van drivers.
The wheels are a mess (bearings? WHAT bearings?), the handle on the top of the bag is history (Too many times walking up the stairs of a jetway with that one handle bearing the brunt of the contents of the bag AND the flight case hanging off the front), and an abrasion on the outside of the bag has turned into a hole... but a small one near where the back of the case comes around to the side of the bag.
But for $69, who can complain? I've seen some of my coworkers' PNS and TravelPro bags that end up in exactly the same condition, and as often as not, need new bags sooner than I did. I dunno, I can't see spending over $300 on a bag when this one has done the trick for this amount of time. This is the same reason I don't have a nice, leather flight bag. It ends up being thrown around enough that I don't want to spend money on that, either. It doesn't help that the Saab has a diabolical bag-piercing metal clip at the end of the bag tie-down in the flight bag "well" next to the pilot seats.
If I flew an airplane where I could keep the rollaboard in the cabin/cockpit, where I didn't have rampies joyously flinging my bag around every leg (or intentionally burying it under 600lbs of other bags, which I suspect they do whenever they see "crew" tags), where it wasn't being abused and subjected to damage on such a regular basis, this bag would easily last a decade.
American Tourister's $70 bag gets my vote.