HN user
This is really useful, thanks for sharing.
Have you actually manually mapped the similar characters for the entire unicode set? It would be cool to have some offline image processing done that identifies related characters to augment what you already have.
The challenges to compete against Craigslist aren't unique to Craigslist. Startups that want to compete with any dominate product in the market pretty much have to face the same challenges. Ebay, Facebook, Google Search, etc. all share similar challenges, specifically solving the chicken-and-egg problem.
However, I do believe that competing with Craigslist might be a bit easier given that there is almost no innovation happening in the product. Craigslist hasn't changed much since I first used it 7 years ago. There is definitely an opportunity to disrupt Craigslist position and it's a matter of time.
Craigslist is in an amazing position right now and they have a lot of potential to really continue to dominate. Ultimately, Craigslist's demise will be through its own undoing of not actually trying to compete and innovate.