Q: Take a common English word. Write it in capital letters. Move the first letter to the end and rotate it 90 degrees. You'll get a new word that is pronounced exactly the same as the first word. What words are these?I think it is a foregone conclusion that Will intends us to get creative with how we write our letters.
Edit: The two hints were "foregone" and "write" which contain hints to two possible pairs. The picture gives an example of how you might write a W so it looks like an E when rotated. By the way, the picture is of a set of Ambigrammic Letter Tiles created by Eric Harshbarger.
A: WON, ONE or WRY, RYE