I agree with most of your points, when I first heard his comments I was surprised too. Like you mentioned we have people Kendrick, Vince, etc putting out thoughtful music all the time so it didn't make sense.

When he's talking about hip-hop nowadays I'm pretty sure he's referring to mainstream "SoundCloud" music. This isn't a new opinion and I'm surprised people thought he was actually referring to Kendrick and other rappers. His wording definitely could've been better though.

The Bob Dylan comment was about his personal preference. He never said that if you want to listen to something meaningful you should listen to Bob Dylan. He was just saying that personally when he wants to cry he likes to listen to Bob Dylan.

I mean I definitely think your points make sense but this is just my two cents on that.