This is very interesting. As a Canadian who had never heard of the poem (only of the term "the road less traveled"), I found it very interesting - though after reading it, I found neither interpretations satisfactory to me.
It seemed, to me, the poem was more about actually making decisions, and not looking back on them - because no one can read the future (just as the person could not see beyond the undergrowth), and either could take him anywhere. Because as far as I can tell, he never actually passed the intersection. The first verse, when he arrives, I assumed to also represent Spring for thematic reasons. The second, when he observes the second path, represents Summer as grass has actually been shown to grown. And he notes that both path most likely have been worn the same.
In the third verse, he denotes that leaves no one had stepped in covered both paths. Now, unless something goes wrong - leaves only fall in Autumn. Note that he claims that he "kept the first [step]" for another day. The last two verses, to me, have a double-meaning - "knowing that way leads to way, I doubted if I should ever come back". I feel it is both a commentary on how much of an ultimatum most decisions are, as well as a story passage where he doesn't know if he should come back to this fork (decision) ever again - which to me also poses as some sort of evidence that each verse happens as he comes and goes to this fork.
And finally, the last verse. To me, the sigh implies a less-than-ideal conclusion. And the fact that he took the "road less traveled by"? In some sort of twisted way... if, in a fork, two paths are "equally worn" - then the way less traveled would be backwards, for most likely very few people actually traveled the path in that direction. And that had made all the difference - and the whole difference being that, since he could not travel both, his indecision led him to know neither path. He had known that fork for presumably a year - but his non-commitment disallowed him seeing further than it. All of it simply because he could not travel both - which implies either that he cannot come back, or can only take that road again - which implies, he has to commit to a change for him to progress.
As a side note, I also interpreted this progression as, in a twisted way, being left behind - by the first verse, the roads are described as well worn. By the second, they are at least grassy. And by the third, it's described as no-one having stepped on them. So his indecision also resulted in him being "left behind" at this decision - while everyone else around him grew, evolved, progressed, he had stayed at that very intersection.
If we were to compare it to pop music (yes I know, bite me and laugh) it's less All Star and more of a warning against Bittersweet Symphony.
Overall, though, 10/10 article. I don't remember the last time I was pushed to read and interpret poetry by an article.