Hello jashley,
Here's my answer. Here are few things that you can check. You can check the Customize -> Tabs -> Customers (Edit Tab Links) -> Estimates -> Edit Roles That Can View and make sure the staff role is checked. Coming to Ship to line make sure you have information entered in the Ship to line filled on Customer screen. You also mentioned that it is also not showing up on print preview. In order to make the Ship to available on print preview, you have to edit the report in Report designer to show Ship to field on print preview. On this link you can find the amazing video tutorials on our report designer.
-Inder