Its seems to me you need to decide what your values and priorities are. If you decided to homestead expecting to keep on pace with contemporary values such as wealth and social status then you made the wrong choice. The choice to largely leave society and attempt what you have is one often made in spite of contemporary values. Its a choice to leave them behind and adopt new values. Subsistence can be enough, if you decide it is. On the other hand if you haven't made those value changes in step with your lifestyle changes you will fail and likely grow depressed.
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