You mean we're all makeup obsessed? LOL - Jen, I can see it now. Red-stained clothing, but emerging triumphantly with the Kisser Slicker!
(I wonder if insurance would cover that?)
Mikie, I do something similar with the colour choosing - I have a couple of Karen's makeup bags, and they're great, but I think I'd need three or four more just to house the e/s collection (I have friends who can't figure out why anyone would need as many as ten e/s's - ah, where to even start?), so I've taken to trying to keep e/s's in large see-thru plastic bags based on the colours - blues in one, greens in another, purples in another, highlights, liner shades, etc. and grab from complementary ones - though when I get new SN colours I do try to co-ordinate so I can write coherent reviews. Can't say I've ever kept a lipstick in my bra, though! And I still don't carry a handbag, even though I have several - stuff just gets shoved into pockets.
Jen, what is this Plano box you speak of? At the moment I'm living in an alcove of a one-bedroom flat that I share with four other people, so I'm reduced to putting on makeup trying to balance a mirror on the bed whilst the cats get into everything - grrr! But it's usually not that bad, and anything to take up less space and keep things organised would be good.