I think she squandered her talents and her career. It's one thing to walk your own path and do your own thing, but she took deliberate steps to alienate her dwindling audience the past few decades. It's been a bizarre thing to witness. I think she's kind of screwed up, but in her heyday she was a brilliant storyteller. She created a gallery of characters in her interconnected songs that seem cinematic.
I kinda agree; however, she did go through some heavy (self-inflicted) traumas in her life, involving drug addiction, financial problems, failed relationships, etc. I love the fact that she is constantly in search of new artistic direction, which makes it particularly ironic that she suffered writer's block for so many years. Nevertheless, I think her body of work up through and including Traffic from Paradise is astounding, reaching her apex with Flying Cowboys. It's sad that she has only released one strong album within the last twenty years (The Evening of My Best Day, and she has largely settled into this grungy-folk vibe these days that is pretty much unlistenable. I really tried to get into her last couple of albums, but... I just couldn't.
One of my favorite live performances by anyone ever: