1) The poem is about taking two different paths in life. One is nicer than the other, which means there is a rough path and a smooth path in life. He chooses the path less travelled, which is the good path. He sighs because he knows to be on the right path, you have to do the right things all the time, which isn't always as fun as being a little rebbelious sometimes. He doesn't regret taking this path, but regrets that he must follow the rules of the road rather than take the bad path and wear himself out just as the path is.
2) People are shaped by their surroundings. If there is a good path and a bad path, and he takes the good path, he could end up with a steady job, happy family and be respected. If he took the bad path he could've got cought up in drugs, gangs or gone banrupt and forced to live on the streets.
Why is the less traveled path the better path? Remember to look at this poem as an allegory.
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