calendar, reservation system

This may be by nature a fairly general question; but this is definitely an area I need to "measure twice, cut once," and get the planning right before taking off on it.

I need to design a calendar/entry form system for booking our video services. The important criteria I can think of are;

• Reservation form accessible by authenticated users (both clients and us)...so clients can request a booking, and we can edit
• fields would include job#, date, time, address, job name, client name, company, billing address, etc.
• we would receive an email notification to evaluate the request and assign a videographer if we have one available
• resulting complete calendar only visible to us (e.g., admin and certain in-house roles); but clients able to view a filtered calendar of just their own bookings
• resulting calendar will show client, videographer, job# and job name (we need to also allow a variation to just show [videographer], "busy" so we know when a certain videographer is booked for an external job)
• automatically assign a sequential job# once job has been confirmed (**this might be the toughest one for me)
• client would be able to take advantage of autocomplete or a dropdown widget to quickly re-enter info entered on previous reservations, could edit any mistakes previously entered...some default info might initially be pulled from their user profile info (phone, email, etc.)
• conditional colors on calendar items to denote status (tentative, all information complete, confirmed)
• email a confirmation request the day before for clients and videographers, preferably with a link for them to click to confirm "the gig is still on for tomorrow" and asking them to verify or correct/update the time/location, etc. (after which the calendar item finally changes to a "green" color indication)
• this reservation form might be expanded later into a "phone Q/A script" for a booking person to operate from, which might branch into other nodes for other of our services
• for *super* bonus points, the relevant client:job info would be able to be imported into QuickBooks Premier or Enterprise

Whew! I think that's the gist of it...if anyone can point me toward the right modules/strategies, I would be grateful...we really need this to streamline the workflow and eliminate errors. I have *some* limited experience with CCK, Views, and the Calendar module, but need to dust off the cobwebs. I have looked at the Webform module documentation also...not sure where to start. Hopefully the above "problem statement(s)" will help someone point me in the right direction. The first thing might be: CCK, Webform, or other?

Thanks so much!