As a designer, Helvetica Neue (even without italics) is a huge step in the right aesthetic direction. His original point was not so much about the font, but about the platform. He lays the groundwork, showing that the platform was higher resolution and therefore it made more sense for a font that displayed better at higher resolutions to be used.
I think it's a valid point and a great critique -- how is it contradictory to praise what is praiseworthy and point out what is wrong?
Or maybe "Of course Ford did forget to include tail fins on this particular model".
I don't think I've seen oblique, sans serif type used in an iOS user interface. Content, sure, and Helvetica is there for you, but this is the system user interface font. I think the clarity demanded of the system user interface argues against the subtle change afforded by slanting the font.
Oblique sans serif fonts are generally sort of an apologetic placeholder for: "Here is where I would have used a nice italic font, but my type designer couldn't pull that off in this clean, minimalist font, so please imagine that he did."
"Ford's new engine is incredibly powerful and well designed, but it's missing a low gear setting on the shifter." Might be more apt.
Again, Neue is leaps and bounds ahead of regular old Helvetica. It's a total bonehead move to leave out italics even though most people won't notice it's absence.
The contradiction is in praising them for their attention to detail in how that made a feature and then pointing out a problem with the very same feature that can best be described as a lack of attention to detail.
In general, yes. They might have careful attention to detail in general but show less attention here or there. But in this case, the feature that they're paying such close attention to is the same feature they messed up.
I think it's a valid point and a great critique -- how is it contradictory to praise what is praiseworthy and point out what is wrong?