I have actually been thinking about your GHB thread the last few days and have some extra thoughts on that: Essentially what you are doing is planning for a three day hiking/camping trip, with additional considerations. What I was going to suggest is that (if you have the time) is to start hiking for recreation, with some occasional overnighters. Use your intended GHB load. You are now shaking out your plans to see what actually works and what doesn't, plus getting into better shape, plus just getting outdoors away from the rat race. You have taken a good step with this trial run.

A few thoughts on this thread: good idea keeping some gear on you separate from your pack, in case of separation for whatever reason.

Two trekking poles is better than one in most situations. If for whatever reason you have to get rid of one, just ditch it. You already came to that conclusion, I think.

Soap: There are numerous soaps and multi-use cleaners marketed to the backpacking crowd that are used for cleaning you, your hair, clothes, dishes, dog, whatever in cold, warm or salt water. Check out REI.

While you're at REI go find the "Shoe Guru" in the store. Based on experience I know that hiking on pavement will chew your feet to shreds, even if you are in shape and have good calluses. This, and "ankle support" are covered by haveing boots that actually fit correctly. High top shoes do not offer any extra ankle support if they don't fit correctly in the heel. Your foot will still roll if the heel isn't stabilized. High top or low top should not matter as long as it fits correctly. That being said I still recommend a higher top hiking shoe/boot for your purposes. They provide better rain protection with your rain pants pulled over the top (assuming you go with a waterproof version), and they provided better impact protection for your ankles. This is a consideration for getting out and through debris from an earthquake, flood waters that you may have to go through with nasties floating around, dog and snake bite protections, etc. Heavy duty, all leather, clodhopper hiking/mountaineering boots are probably overkill for your purposes and as someone else mentioned, save as much weight from your feet as you can. A midweight, hightop, waterproof hiker like those from Merrell and other makers should work fine, BUT GET IT FITTED CORRECTLY BY THE SHOE GURU. For extra fit/comfort/cushion REI will have numerous choices in replacable footbeds. Check again with the foot guru.

Water supply is a personal issue with most people. I have found I like the convenience of the hydration bladder, and I drink a lot more with them than from a bottle. This is a good thing, but YMMV. Having a separate small water bottle on your second kit is probably a good idea for the redundancy mentioned above.

Consider gaiters, also for protection/rain use. Good job. Get out there and keep "testing."