On the "leading" edge of the rudder it really doesn't matter as it's pretty much covered by the vertical stabilizer. It's the trailing edge is where you will see the miss match. I matched the trailing edge, sorta because of the slope.
I used printed vinyl to do it.
Painting would be a pain.
Art
That looks really nice. When you paint the pattern how do you mask? I started to layout my checkers and couldn't find an easy/reasonable way to mask and make sharp corners.
One of the toughest decisions was what size to make the checks. I looked at LOTS of images of RV’s with checked tails before deciding.
Here is one for you older guys...a 3.5 inch floppy turns out that is a good size