As one who nearly drowned in that tar pit a few years back, I have few insights. 1) Your product needs to be an order of magnitude better than your competitors

As one who nearly drowned in that tar pit a few years back, I have few insights. 1) Your product needs to be an order of magnitude better than your competitors in order to get users to switch. There is a reason craigslist, despite its obvious flaws, has not had a serious competitor. 2) If your product is not an order of magnitude better, design will not make much of a difference. Usability can, but not as much as you'd think. Many companies have produced a better evite, but none have gained the traction they deserve. 3) Right now, if you count on local merchants to purchase advertising, you might as well wait until hell freezes over. There's a whole set of entrepreneurs in the world who don't understand the internet and took their hard earned money to open up small bricks-and-mortar stores. Go to a website like Yelp or Menupages (both have substantial local market page views). You'll find almost no local ads, despite the fact that local businesses stand to benefit enormously from purchasing them. I hope you figure it out. Someone has to rescue us from the mediocrity of most local websites. Might as well be you. :-)