I take my IEM's to school everyday. The D2 is in a crystal case, screen facing my body (subconcious). Sometimes the D2 is in a mint tin, or just in the crystal. Sometimes all the gear in the waterproof Livewires box, but most of the time just in the crystal. My livewires are normally in an Ety pouch, sometimes just in my pocket if I stick them in before I leave. Sometimes a mint tin, or with the D2 in the livewires box.
I muck around and get pushed about, but I'm careful as to which side I go down! I check every hour or so probably to check I still have everything, but thats cos I could never afford to replace any of it.
My D2 has been to the beach, in a resealable bag with a hole in it for the wire. No livewires though. Didnt want the sand going in the sound tubes, or from my ear canal (swimming) into the tubes... MX500's for that stuff. I guess I dont go to the limits.
I put my hood up when it rains, and if i'm not wearing a jacket, unless it is chucking it down, I dont bother, however when it is really wet and hoodless I worry about water getting into the earphone connector, shorting etc.
I guess I don't go to the extreme, but my D2, accesories, and LW's and sometimes MX500's are on me everyday, i check they are there all the time, but only because I was lucky to get what I have, and cant afford to replace it at 16.
Matt