It really depends where you are riding, but it can happen quite easily.
I had an'85 FXRS Sport for many years, the belt was quite wide, but both the upper and lower runs were very well guarded. Quite regularly I cleared debris from the lower guard, so it is a fair bet it would have lunched the belt on more than one occasion.
An open belt may look cool, but it is very vulnerable.
I really do like belts, but they need to be used sensibly. Correct adjustment is very important. They give quite a lot when they are bedding in, then pretty much nothing at all for the life of the belt. A slack belt feels pretty much like what you would expect...an elastic band...unpleasant to ride and in a very short time you will have fractured and missing teeth.
Cleaner lighter smoother.
Nige.