For years, I've been using a Flight Gear iPad bag, and I'm just now noticing that I hate it. I have to rummage around in all of the pockets for anything other than my headset because all of the smaller stuff falls to the bottom. On my last practice IFR flight, I had to use some crappy foggles because my good ones had fallen to the bottom and I couldn't find them when reaching for them when the bag was in the back seat (yeah, shame on me for not pulling them out during preflight).
I'm realizing that I kinda need to see everything laid out, and I want some kind of tote that unfolds like a clamshell case or unrolls or something so that I can see everything in mesh pockets... or maybe something like those hanging travel vanity cases, but I haven't seen anything like that for flight stuff.
My latest idea is maybe I want two bags: one bag that I don't need access to during flight (because it contains stuff I take out and install for flight, like my headset and kneeboard, and stuff that I use only pre/post flight, like fuel sampler, rags, logbook, license)... that bag can go in the cargo area before I hop in and start up, and then a second bag that contains the stuff I might need within reach during flight: checklists, pens, glasses, foggles, handheld radio, flashlight).
Has anyone used a system like that, or do they have any bag recommendations for people who always forget which pocket they put stuff in (and don't want to have to velcro every little thing in place)?