I'd reiterate the suggestion of getting something cheap from TJ Max/Marshals and figure out what works for you (or doesn't). Use it for a few months then buy something nicer. If you're traveling a bunch and your nice bag is out for repair you'll have a backup.
If you're on a lot a regionals get a non-roller soft side, if not a roller keeps the weight off your shoulder (and suit jacket). I've got both and what I use depends on the trip/planes.
Also packing aids (bags, folders, etc) help a lot if the TSA wants to rummage through your bag, not to mention separating out items for different types of trips. I'm a big believer of packing folders rather than bundle packing since I can get to the shirt I need w/o unbundling/rebundling.
Toiletry bags; I've looked at a bunch and tried a few but nothing was the right size and nor allowed items to dry out. Standard quart size ziplock for liquids and a plastic mesh bag for loofa, toothbrush, comb, q-tips, powders, etc.