System automatically pick a booking custom dd/mm/yyyy field and add to calendar in Infusionsoft or should i use Outlook Sync?

Want to be able to use calendar in infusionsoft to automatically capture a custom field - dd/mm/yyyy - which is a date for the delivery of a booking and when the custom field dd/mm/yyyy changes that change to cause infusionsoft calendar to be updated.

So for example we get a booking to deliver an event to a location on one or more days, with one or more Deliverers. We have Delivery Date and Deliverer as repeating custom fields on the opportunity eg booking is for 10/11/2018, 11/11/2108. 18/11/2018. The Deliverer can be the same person or different people on the days

We would like to have the system put onto the calendar each of these delivery dates and deliverers. Time - all starting at 0800.
The system to add these to the calendar once the booking has been confirmed.
The system to update the calendar if the date and/or deliverer changes.
Colour coding for the different deliverers - who are held as contacts on the system would be ace.