diademgrove - You bring up a very, very good point. Is his story not enough reason for you to empathize with his plight? Is someone in an impossible situation something you can't sympathize with simply because they've accepted a truth maybe you don't want to consider? I find it interesting that you would feel disdain for or dislike the person just because they have given up.
There is a phenomenon in psychology observed in humans and other animals called Learned Helplessness(
http://en.wikipedia.org/wiki/Learned_helplessness). Basically, it's been observed that if pain or suffering proves inescapable, the subject eventually does give up(loses hope) and simply accepts it. Even if the situation changes later, they may not be able to recognize the opportunity because to them it stopped being a possibility. You would never wake up thinking, "Maybe it will rain candy today." But that might be just as impossible a proposition as escape is to them.
Considering his situation, it is an impossible task to affect change so giving up is pretty reasonable, why hate him for it? Why not be sympathetic to his unfortunate fate? I understand your desire for a happy ending, for leaving the story with a feeling of hope but that is exactly what the song is about, the lack of hope. I also understand if that makes you feel uncomfortable or that ever giving up being sometimes acceptable is maybe uncomfortable for you.
That being said, how much value is there in music that is just sad? I suppose everyone uses music for different reasons and as story tellers we do need to create connection in a way that is rewarding. Then again, maybe your conflict between liking and hating the character is valuable? I don't know. Obviously happy, hopeful songs are always popular and many people seek them out for enjoyment specifically because it makes them happier. Perhaps my challenge then is to try and create empathy for the character without having to change the hopeless reality of his plight.
Thank you for sharing, your feedback is very helpful.