Yes, it's worth it if you fly more than a few times a year: the compression system and durable shell earn back the $275 price over the years you'd otherwise spend replacing cheaper luggage.
I've had my Away Carry-On for going on three years now and it's been through more overhead bins and gate-check piles than I can count. The compression system is the real selling point, not the brand name. I can zip a week's worth of clothes into what's technically a carry-on because that second zipper mechanism actually squeezes the load down instead of just being a marketing bullet point.
The shell has taken real abuse. A gate agent in Denver once tossed it down a ramp onto concrete and I braced for a crack that never came. Two years in, the corners show light scuffing but nothing structural. I have read plenty of reviews from people whose shells did crack after rougher years of travel, so I won't pretend it's indestructible, but mine has held up better than the cheaper hardshell bag I owned before it, which split at a wheel mount after eight months.
Where it loses points is flexibility. There's no expansion zipper, so if you're the type who buys souvenirs or comes home with more than you left with, you'll hit the wall fast. And at $275 for the base hardshell, it's a real purchase, not an impulse buy. You're paying for the compression system, the wheels, and the warranty, and if you only fly twice a year, a $90 hardshell from Amazon will do the job nearly as well.
For someone who's in and out of airports monthly, though, this is the bag I'd tell you to buy without hesitation. The compression system alone has saved me from checking a bag on trips where I'd otherwise have had to, and that's worth real money in avoided baggage fees over time.
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