cutting face at texture wrap i've been looking everywhere for this but i can't find anything at all... basically what i'm trying to do is something like

normal:


what i'm trying to do:


is there any way i can achieve this?
You could: 


Make a flat plane, and create UVs. 
It should automatically adjust to the texture you have.
Duplicate it, and then move it to each side, so that you create that checker board pattern you want.
Then, you could simply create a cylinder and use it in a boolean operation to cut the flat planes into the circular shape you want. 
You'll need to do some extra cleanup, but it should work.