Some of it, some of it you take with you. It's not like a character walks naked into the woods with only a dagger.
No, he has his Explorer's Pack: A backpack, a bedroll, a mess kit, a tinderbox, 10 torches, 10 days of rations, a waterskin, and 50 feet of hempen rope. Plus the clothes on his back, that dagger, and probably a good axe. Maybe a bow and arrows, or maybe you make those. That's what you've got. You could, after quite some time (months or years) manage to set yourself up quite nicely, with a little cabin, several sets of buckskin clothing, and wooden furniture. Perhaps even candles. You could
not have those things after a few weeks in the wild. There's just no way a man on his own could come close to having a "Comfortable" living in the wilderness in that period of time. Frankly I wouldn't consider him at that level of wealth even with that cabin, etc. Modest, maybe. "You don't go hungry or thirsty, and your living conditions are clean, if simple." That sounds like the pioneer life to me.
And yes, fleas and lice don't live in the woods. They live where people congregate. With their is refuse, rubbish and garbage. They are problems with "civilizations" not in the wilds.
Bears don't have fleas? I find that doubtful.
Once more, I will say, doesn't matter. This is a game. Just like most fantasy game maps don't have outhouses or toilets, why do you want to simulate lice?
I think I've found either a typo or an error. The book says that you can live off of your skills in the city and live in poverty, or in the woods as a well-off person. That seems just exactly backwards to me. Very few primitive tribes would be considered "well off" compared to a medieval artisan, in terms of material wealth.
For real life reference; with a hatchet, knife and twine, in one day, you should expect someone proficient to be able to build shelter, bed, a fire that burns 24 hours and water, without much challenge. They should also be able to set traps, probably catch some small game if they have a bow, fish if they have a hook and line, and forage for some roots and berries. Now, extreme environments like high altitude, winter, deserts, etc would change that, but again, that's not really shouldn't be the standard expectation for a game.
Yes, that's about right. Now look at the descriptions in the PHB and tell me which level of wealth that sounds most like. No permanent shelter, only the clothes on your back, undependable food supply (those snares and bow may or may not pay off, and while fish are a better bet, a fish-only diet, supplemented by berries and nuts (if they happen to be in season) does not sound like wealth to me.
Yes, this is not what they show on Survivorman or the other survival "reality" shows. That's because of 2 things; would not be worth a TV show, and often they have artificial objectives to achieve (i.e. find civilization, travel x miles, etc).
Right, that's true. Plus, unless you have the right materials, getting set up takes a couple of days. My point there was mainly that someone with
no wilderness proficiency shouldn't even be at a Poor status.