Farebrowser, created by jimbob, was a great tool for mileage runners -- instantly providing a listing sorted by estimated cents/mile for all fares from a given city. That at least does part of what you're thinking of, and the idea could perhaps be expanded to include calculation based on elite bonuses and such. Unfortunately, it's been down for quite a while now, but you can check out the details at: http://www.moonlightlabs.com/farebrowser.html