- Maildrops: when are they absolutely necessary and when are they a "nice to have?" I figure I can resupply food and gear on the trail, and never had much of a problem doing that in the past. My past hikes have consisted of ramen, wraps, tuna and chicken, Mrs. Dash or the like, peanut butter/nutella, fruit and veggie from towns, etc. What am I missing?
As long as you are willing to sometimes make do with less than stellar choices, maildrops are not needed. Especially with AWOL's guide, you have a good idea of what is available ahead and can plan purchases accordingly without mail drops. That's for food. For gear, if you switch to a warmer summer bag and summer clothing, you'll want to have it shipped back to you around Bennington VT.
- Sleeping Bag: What temp rating should I be looking at for the cold weather months? I'll deal with summer when the time comes, I have alot of experience with that.
I'll second the opinions above.
- Water Filters: it looks like they've come a long way. Should I drop the Katahdin Hiker and iodine tablets for AquaMira and a Sawyer Mini? I'd like to save the money unless its going to save me tons of time and weight.
Depends on the person. AquaMira definitely - there is a much shorter wait to use the water compared to iodine. I'd pick up some AquaMira or MSR Sweetwater and carry the Katadyn with you - you'll quickly find out on the trail whether the pump is worth it to you. If you have to replace the Katadyn, most hikers I know would replace it with a Sawyer.
- Cold weather clothing: I don't like to pack alot of clothes. Can someone explain a simple warm/dry configuration for the colder climates?
My body runs hot. Wool socks, thin nylon pants, a cold weather baselayer (this one: http://www.underarmour.com/shop/us/en/mens-coldgear-fitted-mock/pid1215483-400), thin liner gloves, windproof hat. I hike in that below 30 degrees. I often wear heavy duty mittens until my body has warmed enough to keep my hands warm. A rain jacket blocks wind and offers a good bit of warmth. I also layer a Patagonia nanopuff for short stops (my favorite piece of kit - wind resistant and stays warm even when wet) and a light down jacket (Montbell UL) for camp. I started in April and sent the down jacket home fairly early.
- Cold weather footwear: I'm a New Balance guy in the spring/summer/fall. Is there a solid (dry) option for something more comfortable and agile than heavy boots in the winter?
I don't know of any. I'm experimenting with building my own minimalist winter footwear. (Note: I wore trail runners and would wear them again. My comment is in regards to dry footwear for winter - not what I would wear on another thru.)
- Underwear: my achilles heel was chafing on the inner thighs. I see alot of talk about bike shorts, going commando, etc. What are some preferences?
Ex Officio boxer briefs are great. They are my go-to item. I wear them under my kilt too.
- Ankle support: I have a questionable left ankle that needs extra support. I use soft braces for most sports but am wondering what else people might be using out there
I can't help on this one. I would bet there are strengthening exercises.
- Rain protection: My legs/waist got hammered in the Smokies a few weeks ago wearing a standard rain jacket. Seemed like a cheapie poncho would've done the trick but I'm wondering if there's a silver bullet out there to handle all-season wet conditions.
Ponchos fail in high wind scenarios. For spring and fall, I like a rain kilt but it too fails in high wind scenarios although it worked slightly better than the poncho. In winter conditions I bring/wear rain pants. If you are going the poncho route, consider the Packa which integrates a pack cover into the poncho.
- Stuff Sacks - multiple stuff sacks or one big stuff sack?
Stuff sacks of different colors: one for food, one for clothing, one for stove, one for shelter, and one for TP/hygiene.
- Pack liner - alot of people not digging pack liners, do stuff sacks render them useless?
Stuff sacks are generally not water proof but are water resistant. A simple contractor trash bag or compactor trash bag works great. A lightweight silynylon pack cover is nice too - it prevents the backpack from soaking up and retaining water.
- Insects - is this a problem in April / May NOBO?
At least by the end of May the bugs start to come out. They never bothered me while moving and my shelter's netting was quite sufficient.
Any help would be greatly appreciated!!!