Hi Little Hawk,
I didn't want to leave this thread hanging with no further reply, so here it is ...
Just so you know, I am the person who posted here as a "Guest" before I figured out the signup procedure. I absolutely didn't mean to "pick on" you when I used the word "nonsense". It was the story you heard that I was dismissing - and it is perhaps a good example of what happens when information is passed around as local lore. The woman was definitely not Liona Boyd so I said that and clarified the timeframe; I saw no reason to name the person it was, so I didn't.
Your observation about "whose to whom" is very astute. There is always a lot beneath the surface in a Lightfoot song.
The fact that there was a fellow nicknamed Sundown who lives in Orillia is very interesting. It doesn't change what the song is about, and it isn't about the guy with that nickname. But, Lightfoot thinks in puns and metaphors; can't avoid it - and that is part of his gift. So we can be sure that when he wrote the song, he got a little chuckle out of the fact that "Sundown" had still another meaning (after the literal meaning and as the metaphor he uses in the song). I often say that I am amazed when I uncover still another layer of meaning in one of his songs, and I would say that this is one more example of how very clever Lightfoot is.
It's nice to meet you. Maybe we will hook up at a Lightfoot concert one of these days. Just back from Massey, I am now eying those concerts in Ontario the second week of August ...