Comment by Calavar

I think the discrepancy comes from semantic overloading of the word "should" in "I doubted if I should ever come back." In older style English "should ever" can be interpreted as would ever happen to or would ever be able to but in contemporary English it's more likely to mean would ever want to.

There are other clues for the reader of course. One path looked less worn, but in retrospect it wasn't actually less worn. He would tell the story with a sigh, which isn't something you would typically do if you were happy about it. So I agree that it boils down to most people not being very good at reading nontrivial texts. But I don't agree that that this text is totally straightforward. It's not highly complicated, but it's not everyday text either.