Not going to happen. Craigslist is at that early Google period where everyone who uses it for the first time never looks back and is uber-loyal to the brand. A slick competitor with a great interface and new tools still has to climb that huge Ebay/Facebook-style mountain (no users no stuff, no reason)
What about layering some features on top of Craigslist that are mind-numblingly idiotic to leave out? I'm thinking better meta-data for apartment listings, for example.
no no no no no no.
Craigslist can't scale like google did because it's LOCAL. If I'm the only person in my country using google - I still have value. If I'm the only person in my country who uses craiglist - it's useless.
My local craigslist sucks. There's pretty much nothing there but spam.
Just make sure that when you launch - that you're not targeting SF/NYC.
(I will admit - there is local competitors that you would have to beat in most markets - so it's still tough - but it's not always cl.)
Your interface is cleaner and more attractive, but cycletrader.com is a pretty well established competitor. Do you have a plan for beating them along any particular axis?