Robert Frost’s poem “The Road Not Traveled” presents a man trying to come to a decision about an important, though unnamed question. Your question asks when Frost made his decision. Keep in mind that, although “The Road Not Taken” is about a man struggling with a decision, we cannot assume that this is actually autobiographical. In other words, the speaker we hear was created by Frost but is not necessarily Frost himself. With that in mind, consider the following points about the poem.
The poem was first published in 1916. Frost was born in 1874, so he published the poem when he was about 42. This doesn’t tell us when he wrote it however, because poets have been known to spend years revising their work.
As far as the speaker in the poem is concerned, we can only guess at his age based on the evidence Frost gives us. In the poem’s final stanza, Frost has his character look into the future and wonder how he will feel about his decision:
I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a yellow wood—and I,
I took the one less traveled by,
And that has made all the difference.
The only clue we have to the speaker’s age are the words “ages and ages hence.” This implies that he will be considering the effects of his decision far down the road—years into the future. So we would expect him to be a relatively young man at the time of the decision.
As for your second question, we don’t really know if the road was easy or difficult to travel. The only information we have about the condition of the road is that it “was grassy and wanted wear.” That just means that it was not a frequently traveled road; it doesn’t tell us how difficult it was. The difficulty lies not so much in the traveling, but in deciding which road to take.