A very interesting thread from my point of view, thanks!
I don't know if I qualify, because I don't exactly live off the land, but that is because it is often both impractical and illegal. But I have spent many years travelling from town to town all over europe with no money and no backup, just a rucksack on my back. (For food aquisition I prefer a musical instrument to a rifle!) For many years I carried a tent, but now with time my body's starting to complain about the weight I've been carrying. I tried cycling for a few years, a long meandering trip that took me four years to get from Holland (where I built my bike-trailer) to the foothills of the Pyrenees, via darkest (hilly!) Cornwall. But although I enjoyed it immensely I found that I could hardly ever leave my trailer unattended, so I've gone back to a backpack, but tried to lighten the load.
I've slept rough in dozens of different towns, in a dozen different countries. I'll go into the details for anyone who's interested. For now, to answer the post, when I'm sleeping rough I carry in my pack:
bedding, in this order, from the ground upwards:
A military poncho, folded lengthways, to keep out the damp;
A rather worn-out cheapo sleeping-mat;
An inflatable thermo-rest;
A good sleeping-bag inside an ex-army bivi-bag;
A tarp.
Kitchen (when I carry one) consisting of 206 camping gaz cooker, enamel mug with a lid, cheapo non-stick frying pan, tin-opener, spoon and fork. I also carry an Opinel #7, which is all I think I can get away with if I get stopped and searched, for instance.
Clothing;
Washbag;
Plastic clip-top storage box for a few personal items, maps, documents, and stuff that has to stay dry;
Water bottle;
A cloak of invisibility!
Like many of you, I would love (oh how I would love!) to dissappear into the hills and live on bushcraft skills alone, but as we all know, open fires are (quite reasonably) heavily frowned upon and usually illegal almost anywhere you go. Trapping likewise. You might get away with a fire occasionally, but as a rule it's mostly a no-no, as one of the key points of sleeping rough, as I'm sure you'll all appreciate, is to not draw attention to yourself.
That's it. That's all you need, assuming you have some way to provide yourself with food.
Al.