Sill quite loose however I will give my opinion. Your budget will get you a good bag but may not meet looks good and practical requirement, this is also something only you can decide based on your travel needs. Personally we have had the likes of Tumi, Briggs, Rimowa, Delsey and Brics. I have owned and still own the Tumi and Briggs (although 2 are on ebay). MrsM and MissM have had the other brands as well as other commercial brands.
Just my thoughts:
If you are after brand Tumi, Rimowa, Delsey and Brics are up there with the best. IMO Rimowa (ally) is one of the best looking, however dents scratches and can make it look shabby well before it worn out. Tumi good looking and solid but expensive. Delsey and Brics look nice but we have had issues with wheels.
Briggs - pretty much bullet proof and have an unconditional LT warranty. The external handle system when combined with the internal push down system means you can shove a lot of stuff in a small bag but can easily blow HL limits. The briggs bag I have also has an internal suiter. The criticism I have of Briggs is the raw weight the other thing I do not like is that the front wheels are smaller than the rear and as the suiter is attached the lid and the lid (outside) there is a good sized opening for laptops, ipads, phones it can get front heavy easily and over balance. In bashing Briggs, I am in need of a new smaller size carry on and have decided to go with the Briggs Rolling Cabin bag, a 2 wheeler but solid.
At a $250/$300 price point the main thing I would be looking for is how easily can the wheels be replaced. I have a couple of cheaper bags that have lasted the 6-8 years however within the first six moths of owning them I had replaced the original wheels with asphalt grade inline skate wheels and upgraded bearings.
"Away" luggage just looks like another polycarbonate (Samsonite) from a Chinese factory. Just my opinion.