I have three bags plus a headset case. Standard 22” roller, a luggageworks flight case and a cooler.
Cooler has two ice packs and mostly frozen burritos, grilled chicken, sausage, and other prepared food. Try to avoid hard Tupperware and pack everything in ziploc bags, they’ll pack better. Collapsible bowl and titanium spork in there as well. It has a large top compartment I’ll occasionally throw a battery or other useful things in.
Flight case has a gaming laptop, iPad, mouse, chargers (get the anker 5 port usb charger, it’s a lifesaver.) current book I’m reading, vitamins/supplements, melatonin, Pepto bismol, wet wipes, contact solution/dopp kit, noise cancelling headphones for deadheading, two large battery packs and other odds and ends.
Headset case has backup glasses, a notebook, headset, and pilot docs (I keep them all in a passport wallet, makes it dead simple to know you have all your stuff).
Roller has 6 days worth of undershirts/underwear, running shoes, one pair of workout shorts, a pair of shorts, two graphic t’s, Uniform shirts, Uniform pants, swim trunks and flip flops. I try to keep it light so it fits in the CRJ overhead without much swearing.
After every month or two I clean everything out and trim items out that I didn’t need or use and add items that I do. Overall I’ve pared down quite a bit.
I don’t bother with an iron, I just wet a rag and set the hot iron on top of it before I clean my own clothes.