Christopher, I relate to this so much! I'm actually working on an article right now for The Riff about Aimee Mann--the Queen of Melancholy Music, in my opinion.
Those raindrops, like teardrops, gliding down the window or making unpredictable patterns or gleaming in the streetlight at night were always mesmerizing to me.
Thank you for lifting up the sad music! It definitely has a place, and your insights about the psychology of people who listen to it are fascinating.