I think there is a misconception these days that all that is required to live in the wilderness is having the right knowledge. While knowledge is indeed needed, it is not sufficient. There are a lot of environmental and other factors that will kill even the most knowledgeable woodsman. Since we are talking about a realistic scenario, and not a post apocalyptic one, compliance with laws and regulations will be the largest problem, and it is one that can not be circumvented with knowledge. For example, right now in my state the only animals that can be hunter are porcupine, woodchuck and red squirrel. It has been a long time since I've seen one in the woods. Spring Turkey season opens in May, but lasts only a month. Deer season opens in October and lasts for a month and a half. Depending on the exact area where you are hunting, you may be allowed to use a rifle (for deer) or you may be required to use a shotgun. We also have a three week bear hunting season in November. If you do not manage to secure large quantities of food during those periods and store them for the rest of the year, it becomes very difficult. You have to kill a lot of red squirrel to stay alive.
And the big issue is that you may in fact get lucky one year and take two deer and a turkey, store the meat properly, and have food until the next hunting season. However, the following year you may get nothing. Talk to any hunter, getting a kill is no guarantee. Then what? Living alone in the wilderness without a safety net is a huge gamble. Skills help, but a lot of it comes down to luck.
On top of that, we tend to focus on the wrong skills. I don't know a single person who lives in a rural or wilderness environment in the US who starts friction fires, or even knows how to do so. It is a lighter and gasoline from the ATV that gets the job done. There is little room for purity of skill and tradition when feeding yourself depends on what you kill in the next two weeks.
We often look at half told stories and imagine that we can do those same things. Take Dick Proenneke as an example. Most of us think of him as someone who just went into the woods and started living there. That couldn't be further from the truth. He spent years carrying his gear up to the location of his cabin and making preparations. He had savings that he used, he lived in a friend's cabin while building his over the course of two years, and his brother continued to supply him by airplane for the whole duration of his stay. His experience is no less amazing, and he was as skilled as any woodsman I've seen, but he took a realistic approach to the situation.
These are all things that I will and must take in to great consideration. Everything you've mentioned I, more or less, had in my mind as points needed to be planned out. And you're right about the fact that there is little room for purity of skill and tradition. In the end I might actually do this with a partner and have to rely on some modern tools to survive. I might even do a trial run in a cabin somewhere and live for a while like Thoreau, living on the edge of town and have continued access to supplies, help from others, etc. Or, like Llywd wanted, I might have to opt for a community based communal living project as that seems like the healthier and more productive option. All of this will be planned in time.
I appreciate your detailed and insightful response.
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