Yes, I suspect that it is a bad thing. People who like modern UIs greatly outnumber people who like ones from the '90s.

The most straightforward explanation as to why Craigslist remains king is simple: network effects.

Mind you that you're writing that point on news.ycombinator.com (another '90s-esque site).

Maybe people prefer a "newer" web interface when it doesn't have ads, banners, popups, auto-playing-content, clutter (see yahoo), oversized images, 25 tracking scripts loading, but the lesson seems to be that too simple trumps too complex. An example that gets it exactly right IMHO is gmail.

The OTHER problem with having a nice UI is then people start to want to redesign every year, buy new logos, constantly adapt new design and FE trends (make it flat! make it angular! make it ES6! make it react! now pre-render on the server!).

The "how it looks" of Craigslist is fine, just like HN. The "how it works" is abysmal.

> People who like modern UIs

Even more people like stable UIs.

  People who like modern UIs greatly outnumber
  people who like ones from the '90s.

Maybe initially when the fancy graphics grab their attention. But as they start to work their brains notice the "fancy" less and less and usability takes over:

Just like in games like shooters or Starcraft the pros actually turn down graphics settings - they don't notice the graphics any more so they don't are!

Same as why after a month you stop noticing the wonderful paintings you carefully selected for your home's walls. I haven't looked at mine in years. That#s why we get reddit /r/funny posts where people replace the family portraits in their parents house and then make a reddit post with the funny replacement picture "2 weeks and nobody has noticed anything yet".

Brains are made to tune out anything

a) not new

b) not used

So you end up with Google and reddit as major websites.

I'm not quite sure where that leaves websites like USAToday, but I highly suspect people learn to navigate it despite the graphics, and the design only serves to attract people initially. I on't think it helps retain users once they've been there for a while, except that keeping it stable helps keeping customers.

I know that Germany's top 1 or 2 news website www.spiegel.de (the other one competing for the top spot is a tabloid, bild.de) decided to stick to a much more text-based linear design even after a recent major redesign.

So while a look at actually successful websites doesn't tell us that simple designs always win your claim certainly isn't supported by the facts. Probably not as-is, and when it applies a lot of terms and conditions apply: What kind of people does a site attract? What kind of content do they serve? How long do people stay, how much do they interact with and use the site? Is it mostly "look at" content, or are there many interactions (reddit: lots of "using", USAtoday: mostly "looking")? Etc. I would make the claim the more people actually use a site (interact with the contents - clicking, navigating, writing, searching in the broadest sense, not just the "Search" function, for example trying to quickly find the top comments on a page) the less important the "fanciness"/"modernity" factor. As you use an interface your brain stops noticing how it looks and concentrates on how it feels (for example when it's always hard to hit that tiny "expand" icon on a comment thread right next to a complete different icon separated by only two pixels, how the icons look like will be lost).

I can't think of a single modern UI that I like.

Presumably you're browsing HN using Lynx.

For some things, it is a bad thing.

Apartment searching on Craigslist was so bad for so long, services like Padmapper sprang up to supplement it. Now Craigslist has a similar mapping feature to Padmapper, but still far clunkier.

Their forums were never very good, and have largely atrophied.

Sometimes change is good.