Shipping Notifications and Data Needs

We are running into some roadblocks, has anyone else worked through these scenarios?
FedEx is not being added as the courier to the orders we ship in house. I have to manually touch each order to update the field and get tracking info to the customer.
The purchaser is being sent notifications instead of the receiver. We have club members who have their wine shipped to someone else, and many of the online orders are gifts. Since signature is required the receiver has to know when to expect the package.
There is no easy way (that I know of, may be missing something) to update Vin65 w/out ShipCompliant integration. Other POS solutions offer flat file imports to add tracking numbers and change order statuses.
System emails have no on or off switch. Utilizing ShipCompliant Delivery Tools instead would get the shipping notification to the receiver and would eliminate the need to add FedEx as the courier to each order. However, sending emails from both systems is excessive.

There is a tracking number uploader - but for the flow you are talking about it may just take the same amount of time, just a different path to upload tracking numbers.