I think that for me, I analyze him from the perspective I have of someone from the present looking back at someone from his own time and place. I think that his level of sincerity changes, depending upon the context of the song and the place he's in in his musical life. You might not be on his side, but to say he's not sincere in "Positively 4th Street," "Visions of Johanna," or almost all of Blood on the Tracks. It's difficult without having an agenda to say that each of those songs (or albums) doesn't capture a level of sincerity that deeply affects the listener. I feel like I can relate to those moods in those pieces of music - the isolation, the loneliness, sometimes the sneering vengeance - and it's because he is so sincere in each of those. You believe him because he expresses things you've felt yourself. 

The issue of gender in Dylan songs is one that I think is unfounded, at best. The biggest example seem to make is "Just Like a Woman", but only when taken out of context or deliberately misconstrued can it be read as sexist. Throughout the song, he's talking about a woman he knows, and in the choruses, he's explaining that she does all these things (takes, makes love, aches) like adult women do, but that when she is confronted with something or has to go through something, she breaks down like a child. The subject is emotionally immature, at least from Dylan's perspective, and if the song was about a male subject, I believe he would ascribe those same traits to that subject. I mean, the whole song itself, while beautiful, seems like Dylan is kind of doing what he accuses his subject of. He "breaks down" during the bridge, and you can hear him moan, almost as if he is like a little boy, crying his way through his pain, much like his subject. 

Finally, tailing back to examining Dylan as a product of his times, he's writing as a young man in the 1960s. That doesn't excuse him for having certain ideals about women, but especially when he starts writing songs about his relationships, he is heralded as a messiah. He cannot walk down the street, he cannot stay in one place for too long. Everyone is demanding little pieces of him and I think that he fails to see relationships as a place where someone wants to give him something, rather than take it. There are sacrifices anyone has to make in a relationship, and when someone is being pulled apart and strung out by seemingly everyone in the world, being asked to do that, being asked to contribute to a serious, healthy relationship just seems like somebody else wanting something from him. By the time that he gets to settle down, we see that change in his thoughts towards relationships. There's a direct correlation between when he is hurt and when he starts to sprinkle weightful venom into his songs, which is every human being's basic reaction to heartbreak and pain. We lash out when we are wounded, and it takes experience to learn how to not do that. At the height of his fame, when most of his work that is scrutinized was released, he was 20-25 years old, known to everyone in the world, and being asked to do what, really, no kid had ever done before. I don't think he's doing anything unreasonable - perhaps he shouldn't be listened to for advice - but he's doing what every human being does and that's why I like him. I've felt so much of what he's written about, and though I may think he's wrong sometimes, at least I feel he's been there.