i'm having trouble with the checkout disappearing in the item log page once the check out button is clicked and the return button appearing on the date returned. I have a user class that i made that will hold the list of people that checked out something. Should I not have a user class? How does the view item servlet know that the checkout button from the checkout servlet was pressed?

When something is checked out isn't the boolean you stored in your Item class changed to false (to represent the item is not available) . And when something is returned, it should be changed back to true (to represent the item is available). 

The page could be set to look different depending on whether the value is true or false.