Is Craigslist rotting on the vine?

For a site that gets so much of the credit/blame for killing the newspaper industry, Craigslist is a mess of a product. More specifically, Craigslist's search features are a mess.

Maybe Craig and Jim like it this way. Or maybe the staff has convinced itself that messing with the secret sauce will break the spell. Or perhaps users just don't care.

My gut tells me that users actually do care a lot, and that Craigslist is rotting on the vine. I know people who now dread using Craigslist — a relatively new occurance, I think. A quick look at Compete.com shows that traffic is basically flat during an economic period when you might expect classifieds to do fairly well.

The site has three major problems:

• The site's category structure is very limited.
• The site's search engine is even more limited.
• The rigid geographic boundaries are completely arbitrary.
  

The system works well enough in cities where the number of listings is still relatively small, but here in the Bay Area it's anything but easy to use. One example: the Computers & Tech category isn't divided into sub-categories (Mac, PC, whatever.), so it's impossible to browse. 

Searching for "Mac" produces a different number of results than searching for "Macintosh" -- meaning that there is no synonym dictionary to help users find what they need. 

Geographically, it's impossible to search the South Bay and the Peninsula at the same time without also pulling in the North Bay and Santa Cruz.

Craigslist is entrenched, but the product has now fallen so far behind what's possible that serious competition is inevitable. 

I like Craigslist. I want them to succeed. But they need to get their head out of their sand and fix the product before it's too late. 

Retro is only cute for so long.  At what point does a product go from simple to broken?