I'd wait till training is done and see what the airline will buy for you. My airline purchased my rollerboard and had jepps binders for us. The rollerboard they bought me was a Travel Pro Crew6. The handle broke on my first trip with it and I'm still waiting on the warranty parts to arrive. As for the flight kit, I have a leather one for luggage works. I'd stick with the David Clarks for now but you might want something a little lighter as time goes on. Good luck!