I came across this version and went down a rabbit hole of watching other people react to it on YouTube because I was curious to see what other's depth of connection to it would be.
I think most people of a certain age know it by heart. It was life-soundtrack music for me as a teenager, and though I always loved the song, I don't think I bothered to explain to myself why.
(It could be that the sheer amount of beautiful, poignant music that was being produced during that magical time distracted me.)
The song has three verses telling three different stories. A suicide, an addiction, and having plans fall apart. The genius of it, besides Taylor's sincere voice and beautiful guitar playing, is that each verse can be interchanged to describe the other stories.
The third verse, describing the dissolution of Taylor's first band, is a sublime pairing of the literal and metaphorical. "Sweet dreams and flying machines in pieces on the ground." Band name The Flying Machines, yes fine, but the words apply to the events of the first two verses just as well.
Make plans and watch the world dismantle them. Try to control the events of your life and realize you are helpless when alone. Assume the things you love will always be available to you.
"Lord knows when the cold wind blows, it'll turn your head around."