We Fly So Close may indeed be one of his most underrated tracks, such as Both Sides as an album. When the album came out many years ago, I was in a really strange mood. My frist longer relationship didn't work anymore and I wasn't too pleased with my job situation either. Some family issues on top and I found myself in a strange mixture of frustration, lack of hope and looking for the right way. Both Sides had this special "down" feeling and it quickly reached my emotions. I will always like this album, but I would never say it's his "best" record. It may be his most important record for me.
Although I can't complete relate to your situation, I was also going through some crappy stuff in my life in the last year and found solace in the Both Sides album. I was listening to it a lot to help ease some of the hardships that were going on. I now put this album on the same level as another dark album that was always helpful to ease the challenges of life, Eric Clapton's Pilgrim album. Not sure if anyone here ever listened to it, but it is definitely a different style EC. And yet the lyrics and especially the music, like Both Sides hit me in many ways with the crap that was going on in my life.