Online Quote – Conceptual Questions

So I have a couple questions. Before I can ask them, I’ll explain my situation. I’m building a site for a small moving company. On this site I need to set up an online quote feature. This feature would allow a user to enter their address and their destination address, providing approx. travel time and cost. Users could then construct an inventory using something like this moving calculator, which allows users to do a preliminary walk through of their home and list all their major items. Users could then enter their home size and density (how full it is with misc. box-able items). From these two components, an estimated man hour count and cost/box count/needed truck could all be provided. For the last component, I need to set up a calendar feature which would allow the user to see the schedules of the movers employed by the company, and also allow the user to request open time in the schedules for appointments (estimates and moving). Finally all this information would be gathered on the final page of the estimate to show the user all the collected data, a rough estimated total cost, and an estimated date/time of completion. The completed estimate then needs to feed through and email to both the user and the company.

Sooo, questions:
1) Is WordPress robust enough to handle this, or should I look at Joomla or Drupal?
2) If WordPress can handle this, should I be looking towards stringing together widgets for my different needs? MapPress looks like it could do that first bit, with some tweaking that is.
3) Any advice? What should I be looking towards? Any other models you know for this type of service?

Finally, thanks to all y’all who read and respond!