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. What I do depends largely on who I go with…as well as when and where I go. 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…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 hiking the AT in three months.
My general philosophy is: less work and cheaper > more work and expensive. There are of course many exceptions...for example...I will often take on additional work to improve the quality of my food and/or pay additional costs to gain a better night's sleep…but as a rule I generally like to keep things easy and cheap.
I also like to keep things very light...but I am not a half toothbrush and polycro-tarp kinda guy. For example...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 for me...but there is a point at which I think light becomes less fun.
I am a camping-knowledge omnivore...meaning I try to learn from all those who sleep outdoors...not just the folks who do what I do when I sleep outdoors. For example...I am not much into bush-craft...but those folks specialize in wood processing and fire-working...which are useful skills for anyone who stays outdoors (at the very minimum for safety reasons). I could go on and on...but simply put...being open to how others sleep outdoors has a lot of advantages.
I do not consider myself a gear-head…I research gear because it is the rational thing to do...not because I particularly enjoy it. Still...over the years I have accumulated a lot of stuff...and I am a little self-conscious about it. In my defense…I buy only a few items a year…and have been sleeping outdoors for a long time...so it is not like I have a problem (said defensively).
Seriously...It makes sense that a thru-hiker or beginner would want a small versatile system for all conditions...but for someone who is buying a 2nd and 3rd shelter/cook-set/etc...it is best to start thinking about creating a synergistic system from which to create several specialized sub-systems. For example...I currently have two cook-sets...the first is a small solo pot (800ml)...the second is a larger (1300ml) pot. These two pots give me a lot of different options together because each pot is light enough for solo backpacking...and yet together they work great for larger groups and complex cooking.
The point of all this is to say that I have a lot of gear because of what it allows me to do...not because I simply like gear. I will discuss and research gear because it is important to the way I have a great time...but outside of the purely practical concerns for having a great time (i.e. sentimentality/style/etc) you will probably lose me (though I swear I am not a robot either).
Though I have slept outdoors in many places…I very much have what I would call a home-region in which most of my experience is grounded. This home-region roughly stretches 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. For me...water tends to be readily available and plentiful...but so much so...that it can become a serious problem (flooding/hypothermia)...so both of these factors shape my opinions and 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 still looks nice next to down.