1.) The speaker may not necessarily believe that they have taken the "wrong" path, but instead they are cursed with a feeling of wonder. " the grass is always greener on the other side" He regrets that he is but one man, and that he will not be able to back track and venture out onto the second path. No matter which path he had taken, he would have been left with the feeling of doubt, the same feeling that anyone who has mad a difficult choice will feel.

2.) The path is symbolic of any choice of great significance, to go to war, to have an abortion, to go to college, or to drop a nuclear bomb on Japan. Any of these choices will lead to many more choices and thus many more forks in the road. Frost is not literally speaking of a road, but symbolically representing life and the many different paths one can take. Furthermore, the speaker knows that although the paths appear very similar from the fork in the road, he notes "{[I]Looked down one as far as i could/ to where it bent in the undergrowth;" he mentions how far he can look down the path, but in truth the path will bend and twist and he knows not where it will end or fork again. This unknowing factor is Frost bringing the essence of luck to the choices of our world.

Fight and Flight
The Road not Taken is an important and well known poem, it obviously applies to a choice made along the path to heaven, and one of the oldest and most important choices people are forced to make is whether or not to fight once confronted. Imagine President Truman's choice whether to drop the bombs on Japan. He probably wished he could know how either path would end, but there was no way of knowing. The poem says "I shall be telling this with a sigh/ Somewhere ages and ages hence" sigh is possibly the most debatable word in the poem, besides the closing line. Sigh i take to have a negative connotation, as in after getting a short ways down the path he starts to believe he has taken the wrong one.
If like Apple Picking, frost is referring to himself, than perhaps the diverging wooded roads was his choice of becoming a poet? Obviously he took the road less traveled and became a poet. At that time he could not be sure he could even feed himself off of a poets wages, the choice of fading into the rows of normality the safe choice, or stepping out into the spotlight of greatness and perhaps dying of hunger, could be a hard one.

I went with truman because shelby didn't like my poet idea =(