How do other people handle multi stop buy shipments in OTM?

We are trying to send accurate pickup and delivery dates to our suppliers and customers on our buy shipments. We have taken our training environment and turned on conditional booking and set the servprov's up for conditional booking. We have added the SHIPMENT_STOP-PLANNED_ARRIVAL and the SHIPMENT_STOP-PLANNED_DEPARTURE to our conditional booking profile so that the carrier can enter a shipment start and a shipment end date, but we aren't sure how we could deal with the stops that are in the middle of these points. Has anyone else dealt with a similar issue with dates? Is there a better way to do this?

We are using 5.5. CU2 currently, and are testing CU3 with hopes to move it into production in the near future.