WordPress And Google Maps Geo Social Based Website

Hello, I’m working on a website (wordpress + buddypress based) and following there are the things i need to be done:

– I need a map where users can choose from text field with auto suggestion (ajax) the “start” , the “end” point and a date (future date). The destinations/starting points should be airports, so you should figure out how to grab them instead of inserting in one by one)

– Every route should count the miles/kilometers (for example from Milan to Rome 500km) and be added to the profile of the user, and showed a PATH in the map (as crow flies)

– In this route, visibile on the map, or on a list, an other user should be able to “check-in”, it’s like an event and then listed in the profile as “attending event xxx”.

Note- i need only a map, not multiple maps, i need a map where there are multiple pins of the various users, registered users.
hope you understood what’s in my mind, feel free to ask me further details and PLEASE show me your previous works about google maps.

I wold like the map like this on on the site http://www.citysourced.com/default.aspx (so with slideshow of the markers with description and list on the side, but a bigger map as the work i made in my temp website here http://www.meletta.net/flywithme , i dont have time to code further 🙁 )

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