if it's going to deform or be smoothed then yes you'll need to make the faces 'squares'
i'm pretty certain though you can't add the edges after that boolean. maya will complain at you saying you can't add an edge that ends or starts at a hole.
that's a "Ch" pronounced as a "K"
Computer skills I should have:
Maya, XSI, Photoshop, AfterEffects, Motion, Illustrator, Flash, Swift3D