I know there are a lot of older questions about this but couldn't find anything within the last year and from skywest pilots. I am buying my luggage and decided on the kirkland bag (just can't justify spending the $300+ on a LW or strongbag) but what else should I look at picking up?

I've heard of flight cases, but skywest has ship sets so are those needed? Coolers, what do you recommend? where do you put your headset?