The question about whether we regret, or take pride, in our choices reminds me of the amusing poem by Robert Frost; "The Road Not Taken."
In the poem, Frost concludes
"I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference."
Now, most people assume Frost is saying that taking the rare road made his life special, but that is false.
In fact, Frost tells the story with "a sigh," because his real point is that we make our choices, and it generally makes no difference, because every choice has its ups and downs. You pick a road, you live with it.
And Frost used to laugh about how people would selectively quote his poem to prove the opposite of the point he was making.
I'm not sure whether Frost was right or wrong, that most choices don't really matter, but I do think it's funny that so many think he was saying that they do. :)
Again, it is the art of something. The meaning of it from the artist's perspective is irrelevant to that of the audience. People hear what they want to hear, (sometimes but rarely, what they need to hear) and it will cause them to shift a little from their path.
I think the sigh isn't bout it no making a difference, it is lamenting what was the cost of taking a particular opportunity. What was down the the road? The road less travelled is not important because it is less travelled and on the road that has taken many feet can be found diamonds that the crowds passed by.