This idea may be far fetched but how about a section of "booking flight strategys" part of ddms? This may be one of my biggest flaws. Start off with simple and popular routes. NYC is probably you're biggest audience so I'd say to start with flights NYC-FLL, NYC-TLV, etc. and a breakdown to which sites and mileage programs you check first, and what to do with no availability... It should be fairly simple when a newbie is looking for a specific route so he or she would navigate to the post with that route.