Your friend with the headaches may be in for a very rough time. Avoiding caffeine and alcohol are critical. On my trip home to 9000ft last summer (from 500ft), I was breathing hard, headachy. Day three I ate a big ole steak and felt great! My theory: the iron helped my anemic-tending body get some red blood cells going.
More cheap rain gear tips: a couple of plastic bread bags for your feet. Pack down much smaller than booties. Put 'em on over your socks. They form a vapor barrier and block the wind. Your feet may get sweaty-wet, but they'll be a lot warmer than they would be otherwise.
DH carries a shower cap to put on over the helmet and has used it. I've been packing one around for years and never had to bust it out. I have used the bread bags, tho!



! My theory: the iron helped my anemic-tending body get some red blood cells going.
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