Best option: Buy everything with good quality and good warranty, and be done with it. I find the best values to lie in B&R and Red Oxx. (You can still save money by purchasing from sales, discontinued models/colors, etc. Scan eBay, Sierra Trading Post, google shopping and other such portals.)
Next best option: By your checked bag(s) as above. Buy a cheaper carry-on; it remains in your care and perhaps need not be as well made. Just make sure it never gets gate-checked!
A special high reward/stress option: Don't check bags. Get by with the best carry-on you can afford. This lifestyle is not for everyone, but does have its own rewards as well as stresses.
If you fly more than minimally, there really isn't any other option.
