Multistop 2 day depot shipment with pickup back to depot

Summary: We are beginning to start testing our multiday depot shipments where the driver is out for 2 days making customer deliveries with their "rest" being shown.

Content (required):

We can properly model the shipment only when we are making delivery stops. However, when we plan all orders and order that is a pick up, OTM will not allow for that pick up to be allowed on the shipment with customer deliveries. OTM will also show the driver leaving earlier than the other shipment with customer deliveries. Is there some planning parameter/ multi stop config that we should have to make sure that the shipment being generated look to create 1 shipment rather than 2. Is this related to the rate service being used that "allows rest" and OTM