The complaints will happen when that simplicity impedes information flow. It's not a matter of visual aesthetics, it's a matter of usefulness. CL's design impedes its usability, independent of its aesthetics.

In Craigslist case, there are clearly better ways to browse housing spots than in a list of links with non-standardized location information in the linktext. In Reddit and HN, part of the joy is serendipity...you don't need to aggregate the content behind each link at once...because of the voting system, you don't worry that clicking on the top link will be a waste of time. That's not the case with CL's chronologically ordered list.

Reddit has made some concessions with allowing thumbnails of image-based posts to show up. Otherwise, its minimalistic approach serves a real usability purpose and is not simply the result of stagnation.

Uh... picture subreddits are 75% of reddit's frontpage traffic and my little startup thinks that there are better ways of browsing pictures than a long list of thumbnails where the title is even larger than the thumbnail preview.

So, you'll be competing with Pinterest?

No. Pinterest is more tuned towards sharing pictures with people that you already know.

Picc.it is tuned to sharing pictures with people you don't know, but share your interests.

Think of it as the difference between glomping onto a pre-existing community (e.g. Facebook friends), and creating a new one (e.g. Reddit).

You can criticise the design of Reddit a lot, but you can't criticise the UI. It works brilliantly.

I guess designers could criticize its visual aesthetic, which is pretty austere, but design is how it works in addition to how it looks. I'd say reddit's devs have shown an interest in improving their interface and making it easier to use over time, whereas craigslist has not. You still can't browse apartment listings on a map, which is the reason why the Padmapper thing blew up so big.