Why improve anything? Because by doing so, we find what really should be.
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.
I like to use the parent/old person test for ui usability(obviously not every old person will do, you know the type tho). I showed my parents reddit and they picked it up right away. Both failed to learn snapchat and struggle through most "modern" websites.
I blew their minds when I showed them if they click the three lines on lpta of websites, really a hamburger menu, they get options and stuff.
Often users are just expected to know these "design paradigms" like symbols(hamburger menu) or which direction to swipe(im still guessing half the time Snapchat). Whatever happened to using words like settings to open the settings menu. When did GUIs' forget to show available commands to users in an understandable format.
Everyone has a huge bias for what they already know. If you already understand and like Craigslist, I'm sure it's great. As a new user, it's awful.
Can you give some examples of the hours you’ve spent being confused?
It may just be a different way of thinking for different people situation. For me, I prefer simple and honest vs pretty wit targeted ads trying to divert.