In as few of words as possible…I would describe myself as someone who likes to go to remote places and stay there for days or weeks at a time. Typically this involves a backpack…a kayak…or a canoe…but I sometimes stay in one place and focus on an activity like fishing…or perhaps camping itself. I would say I have a lot of solo backpacking and paddling experience…but this is due to the fact that I like to sleep outdoors more than most of my would-be companions…not because I prefer it. So while I can certainly speak to the needs and concerns of soloing…I would say that my perspective privileges what it takes to get others to come along on a week-long 100 mile adventure…more than it does the demands of successfully thru-hiking the AT.
My general philosophy is: less work and cheaper > more work and expensive. There are of course exceptions...for example...I will often take on additional work and cost to improve the quality of my food and sleep…but as a rule I generally like to keep things easy and cheap.
I also like to keep things light...but I am not a half toothbrush and polycro-tarp kinda guy. I like Cuben over sil-nylon for tarps because Cuben does not absorb as much water as sil-nylon...not because Cuben is lighter (the weight savings are not particularly cost effective). Keeping things light tends to make everything from backpacking to canoeing more fun...but there is a point at which I think lighter can become less fun.
I try to learn from both the folks who do what I do outdoors...and also the folks who do very different things than I do outdoors. For example...I am not much into bush-craft (I prefer walking and looking over building and gathering)...but those folks spend a lot of time processing wood and working fire. It is unlikely that you will catch me building a primitive shelter...but wood-processing and fire-working are very useful skills...I use both for cooking and comfort frequently (time and weather allowing)...and though not completely reliable...fire could improve a difficult situation.
I do not consider myself a gear-head...I research and discuss gear because it is the rational thing to do...not because I particularly enjoy it. Over the years I have (self-consciously) accumulated a lot of stuff...but I have a lot of gear because of what it allows me to do...not because I like having it like a museum. In my defense…I only keep gear I use...I buy only a few items a year…and I have been sleeping outdoors for a long time...so a large collection is okay...right? For the most part the fact that my gear collection is more reflective of a hobbyist rather than a beginner or thru-hiker is not particularly relevant...but I thought I'd mention it since I probably do have more to say about the purchase of a second cook-set than I do the purchase of a first one.
Though I have slept outdoors in many places…I very much have what I would call a home-region. This home-region stretches roughly from Missouri in the West + Tennessee in the South + Virginia in the East + Wisconsin in the North. Though not perfectly accurate...I would say I primarily spend my time in and around heavy woodland and karst.
Some of the more present features is the abundance of both tree-cover and water where I live and play. For me...tress and water tend to be readily available and plentiful...but so much so...that they can become serious problems (hypothermia/flooding/navigation)...so both of these factors shape my perspective on choice of shelter + rain gear + hats + etc.
Finally...I really do not like to sleep outdoors when the temp is below freezing...at least not without an external heat-source. I still know a lot about cold weather...but not the snow-cover for months at a time and 20-30 degrees below freezing variety...my expertise is more in the area of near freezing sleet with high winds...so for me fleece is still cool.