2010-07-26 Match Play Answer

The question here is should you split your back checkers, and the answer is YES!  Ask yourself, "If I don't split now, what is likely to happen?"  You will either get stuck on your opponent's ace point or you will be forced to split when your opponent has even more ammunition to pound on you when you finally do split. 

People are afraid of being pointed on or hit loose...first, if your opponent makes the 4 point it's going to hurt whether you split or not; and second, if he hits you loose,. a) you might hit him back, which is terrific for you, and b) even if you don't hit him back, he might not cover.

Another reason it is right to split is that when you consider the "upside" and the "downside" of the alternative plays, you simply have more "upside" and fewer "downsides" to the split.