I think you're making some assumptions here based off of exposure to some falsehoods. For one, "comfort" is sort of relative and subjective. I can tell you, I am often MOST comfortable when I'm out in the woods. No traffic, no people, no pollution, no red tape, not of that BS. I'm responsible for my own well being, full stop, and there's a tremendous amount of comfort in that.
Yes, exactly! That's what's confusing you. You're "comfortable" by your own standards in the woods, therefore you assume that that must mean that you are "comfortable" by D&D standards. However, there is an
objective standard of wealth that must be met to be "Comfortable" by the PH, and it has
nothing to do with subjective comfort. It is thoroughly possible to live in a "Comfortable" situation and be miserable, to hate being cramped in a well-appointed inn room, and to long to be elsewhere. No matter; you're still "comfortable" by D&D standards. It's the word itself that's throwing you off.
I know how to make temporary bedding that is just as comfortable as any bed you have, and that's just on the fly (I live in Oregon, so plenty of Douglas fir, etc). I know how to make shelter and how to make a fire to maximize heat, keeping me warm all night long. Food is never an issue here if you know what to look for, from mushrooms, to tea from dandelion root or pine needles, to fish, to squirrel, to birds, to herbs, etc, etc. I can make a meal that rivals just about anything I make in my home with what I find in the woods. I know what plants keep the bugs away. I know enough about natural medicines to rival anything you'd find in a medieval town. I know how to make glue from the bark of a birch tree or pine sap, and how to carve spoons and dishes, and tan hides, and make lamps with an old can and tree sap, and make a mud oven, and any number of things you might think you can only get from a store.
I quite believe you. And that sounds like, after a few weeks/months of work and getting your shelter built, you could live at a Modest standard of living. Perhaps, after several months, you could have a permanent homestead with hand-carved furniture, candles, several sets of clothing, and a nice roaring fireplace over which you can cook varied and interesting meals, which sounds like it could qualify for Comfortable. But living a Comfortable life in the woods after only a few days or weeks? Just not possible, unless you happen upon some well-appointed abandoned homestead. The housing situation alone prevents that. Unless you luck out and find a perfect, dry, uninhabited, fairly deep cave, you will, at the very least, have a much more unpleasant time during a stormy night than that gentleman in the warm dry inn room.
And I can also feel a whole hell of a lot more safe out in the woods than I could in any room at an inn in a town or city where break ins, muggings, disease, loud neighbors, etc are all at. I know how animals behave and can take measures for that.
And yet the PHB doesn't mention
anything about "feelings of safety." What it
does mention is
legal protection against crime, which the outdoorsman completely lacks. If a couple of brigands comes upon his hut while he is away and steals all his stuff, he has zero recourse, except perhaps to try to hunt them down and kill them himself, even if he knows exactly who did it and can prove it. They can waggle his stuff in front of him, and he can do nothing. Not true of that artisan in the city.