I rolled a Luggage Works Executive 22inch for about 5 years. Loved it. $199.
That said, I would consider something else next time, perhaps a Briggs and Riley.
As for the headset, AvComms from PPL days got all the way to upgrade. No probs. Best advice is to not go overboard, try out others stuff, see what you like.
That said, the Costco Kirkland Signature bag does seem to hold up well.