His prediction is that a machine will pass the turing test in 2029.

And yes, there's evidence of incredible machine learning discoveries all around us. You'd have to be willfully blind not to see those. AlphaZero in Go & Chess, the protein folding miracles of Deepmind, all the amazing work being done today. The field is racing ahead. Human minds are good at seeing linear progression. Our brains aren't particularly good at exponential growth, which is what is happening in this field.

He has timeliness on the optimistic side but people were skeptical of his claims in the 80s that a computer will win at Chess by 2000 or that the internet will become ubiquitous. He did think a US company will reach 1 trillion $ by 2010 and that speech recognition will be more widely used but even in cases like that he wasn't massively off.

As far as I can tell for decades he's been consistently more right than his critics and often on issues that are a lot harder to get right than simple coin tosses.

He's been right (approximately) on how fast the tech improves. That doesn't tell you anything about how likely he is to be right about the singularity, though, unless you think he actually has a handle on how much tech would have to improve to get us there, which means that he would have a handle on where "there" actually is, in technical terms. I don't see evidence that he (or anyone) has that.