IMHO- It is easier to do a checkerboard when you paint the entire floor white
first and then tape off the squares. Find the center points of each wall and mark it off. Mark the size of the squares you want along the wall starting from the centerpoint. Tape off on
both sides of the mark side by side. Cut away and remove the tape from the
inside of the squares you want to be black. Paint. Removing the tape carefully- some "schools" say while its still wet so it hasn't had time to leach under the tape. Do this if there is a solid edge and the paint/coating you're using will not run. Some say let it dry to take free and pull it at a 45* slowing and scoring it with a razor knife where needed. Either way I'd reserve small amounts for the invariable touch ups that may be needed. Cover the entire area in a clear coat for an easy transition between the colors.
I find this to be the easiest way. Some people tape off and paint individual squares.

I find less bleed and sharper edges if you are coating one color over the next.

Good luck with the project! It is a lot of work, you should have a helper, and use a high quality low tack painters masking tape, but the results are well worth the effort!
