Is there a keyboard shortcut to add another assignment to a day?

Yes, there is!

When editing the Lesson Plan for a class, if you want to add more than one assignment on a particular day, do this: After you type in the description of the first assignment, hold down the Ctrl key and press Enter*.  That will create a new row for another assignment on the same day.

* – on the Mac, the keys are labeled Control and Return.