Niche Route Optimizer Mapping Website

Website wanted to to create random and user-generated bar routes. It would be simple and could use either the Yelp API or Google Maps API. Basic Functions: Users input a starting point and ending point and the number of stops they want. They can then individually select bars from a list of bars in the area that are loaded from either Yelp or Google's database or select randomize, which will spit out the selected number of stops and put it into a route. If they choose random they would be able to edit the selections after. When finished with the route it would be presented in a nice printable format, which would include 1-2 ad blocks on it. After the route is created a user can share it on facebook, or twitter. Users are forced to sign up to the site if they want to plot over 5 stops or when they want to save a route. Aside from this would be a small news part of the site, and potentially a few other boxes for ads or to promote the most popular created routes. Users need the ability to search created routes as well. For instance, they could search by city, zip code, or something that starts near a point or address. I'd like this all to be really smooth with no real load times, the key is it has to be intuitive. Perhaps in Flash or something similarly smooth. I can give more details to the winning bidder. Ideally I would like someone who has some experience with iOS as well as this will eventually be ported over to an app. Please bid, blank bids without questions will be deleted. Please estimate time it will take as well.