Here's the thing though - generally speaking, I don't know of many people who are confused by Craigslist. It's an effective design for what it needs to do - browsing is easy and obvious, searching is easy and obvious. It's just "ugly", which is a different thing.

I will say Reddit is a bit of a different beast - there's too many hidden and confusing features, and it's probably fair to say that iterating on the design was necessary.

My biggest concern is that what I've seen from the redesign seems to be focused on making Reddit less ugly than making it more obvious and functional.

We're both posting on what might be one of the "ugliest" discussion forums on the internet - but I've rarely been confused as to how to do something on HN, which I can't say for many, many "modern", "pretty" websites.