It's amazing what you can do with monokote with some practice. I have done checker board schemes as well, but on an open structure wing. If you go to my gallery there is a picture of a "Winglet" flying wing that is tapered and swept back, so the checker board is too. The checker was added after the wing was covered, although I have used the pre-made skin method as morris mentioned previously with good results. If you do go to my gallery, have a look at the "Monosport" while you're there. It's done with monokoat also, including all the lettering and numbers.
I use thin cardboard (art board, bristol board) to make templates for all the trim, letter & numbers. I tape a piece of monokote down to a cutting mat, position the card template on top (sometimes with tape as required) and carefully cut around the template with a very sharp #11 blade. I use another piece of cardboard for the cutting mat. Surprisingly, the white numbers over the black wing look great. They are far enough away from the white scallops on the leading edge (which are not over black, just balsa) that you don't notice the very slight color difference.
I have found that like most other things, the success of a good monokote job requires a lot of thought and planning ahead.

Cheers, Nigel