The problem here is twofold.
Predictive statistics work best with large data sets gathered under relatively stable conditions. Bob is a single individual. If Bob is 23 years old and you had data for all 23 years of his life, that would be a lot of data, but his situation would not have been stable. It is unlikely that he was arrested at all while he was under 10 years of age. Moreover, if he keeps getting arrested approximately every 3 months, he is going to be spending all sorts of time in jail, where his arrest statistics will necessarily drop.
Lesson to learn: there are a lot of statistics out there that are worthless for predictive purposes. The data may have been gathered with great care, and the computations may have been done perfectly, but the results have little predictive value. Quantitative data are superior to qualitative data only in certain special circumstances.
If I were asked to think quantitatively about Bob's future, I'd be gathering data about a large group of men with frequent arrests in a short period of time and distinguishing between those who were incarcerated and those who were not. It is a lot easier, however, to think about him individually in a qualitative way: unless he changes his ways, he is probably going to be incarcerated in the not too distant future.