Thank you for taking us along! Looks like you had a good time, got to test some gear, and test some ideas, all in a beautiful environment. Can't ask for more than that!
About keeping stuff dry...what works for me is one thick trash bag in the very bottom of the pack in which i compress the quilts as much as i can, then twist the top and fold it over to prevent air and water getting in. Then on top of that goes bag number two, for hammock and extra clothes. Everything else can get wet...tarp, raingear, foodbag, stove,....and so those things can go on top. 2 bag system.