I am a starter upper based in Chicago and I currently use the facebook places API for finding places near me. This is suitable for some purposes but FAR from adequate for what I want and my customers need. So, I have started researching how to use osm data for searching interesting places near a lat lon or within a bbox. Most searches are for specific types of places (such as coffee, restaurant, museum etc).
So, what should I do? Should I build my own map database from the planet file? if so, should I use xapi or should I use overpass? Alternatively, would you recommend any cloud hosted services such as Mapquest or Cloudmade?