ANSWER
My solution to this problem was to create my own PDFAnnotation subclass.
var isChecked = false
init(forBounds bounds: CGRect, withProperties properties: [AnyHashable : Any]?)
override func draw(with box: PDFDisplayBox, in context: CGContext)
I used the isChecked property inside of the draw function. If the property was toggled on, then I was display a checkmark image I found on Icons8. I also had to add the PDFAnnotationHitObserver in my ViewController, and handled updating the property of isChecked.
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