The Optional checkbox in the data model inspector has nothing to do with Swift optionals. The checkbox determines whether or not the attribute is required to have a value.
If you deselect the Optional checkbox for an attribute, you must give that attribute a value or you will get an error when saving. By selecting the Optional checkbox you can save without giving the attribute a value. Suppose you have a description attribute that's a string. If you select the Optional checkbox you could leave the description blank and still save the entity.
Here's another example. Suppose you have text fields to let a person enter their home, work, and cell phone numbers. These phone numbers should be optional attributes. You wouldn't want to require someone to have a home phone number, a work phone number, and a cell phone number just to save the person's data.