I'm not informed enough to comment on his actual predictions, but I've heard him defend himself. His response to criticism that I've heard is, "my critics are uninformed about fact X," but he doesn't make an attempt to justify X. That approach strikes me as disrespectful and intellectually dishonest, as it's a tactic used by many hucksters and snake oil salesmen. I have a limited understanding of his positions, but the way he presents himself makes me uneasy.
I also think it was elitist of me. A lot of it was just because he's published books that have been marketed as pop-sci trade paperbacks, but I never actually read any of them.
The analogy I always use is a long straight flat desert highway. If you stand in the middle of it and look down its length, it appears to converge to a singularity in the distance. If you can see mileposts, you might even try to estimate how far away that singularity is.
But if you drive toward the singularity, you'll never run into it. It recedes before you. It is just a trick of perspective.
Basically all the talk of how crazy life will be after The Singularity is like trying to explain how crazy life would be on the other side of a rainbow. Fun, but not actually useful.
My point is that this is just an assertion, not a prediction. Every future development to some extent obscures our ability to predict the future of human culture. Look far enough into the future along any line of inquiry (legal, artistic, religious, energy, biology, etc.) and there is a singularity beyond which we cannot predict. It's just a function of trying to predict the future in general, not some special property of AI.
The same cannot be said of self-improving AIs. Kurzweil's Singularity is not about the difficulty of long term predictions, it is that the progress function may become so steep that even short term predictions become impossible.
Which I think is the point.
Also his whole "I'm going to eat magic vitamins that will keep me alive forever" thing.