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I know he is from New England, so any help will be useful to help me understand the poem "The Road Not Taken" and others when taking into account his place of bith.

What an interesting question!  Frost himself was hardly poor. By the time of the publication of "The Road Not Taken" Frost was already well-known and successful.  Yet, at his heart, he was a yeoman farmer, committed to the land and distrustful of success and celebrity.  The lines in the poem echo this dualism of sentiment:

And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth.

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;

One might interpret these lines to mean:  what if I had not become successful?  Would my integrity as a thinker/philospher/poet pay the bills?  Perhaps by default, the poet succumbs to the latter, and cannot clearly say whether fame and sustenance is worth the price of seclusion and the privacy of thought.