The people who benefitted the most from the rule of caudillos were the caudillos themselves and those who supported them. The caudillos were typically not that interested in ruling for the benefit of all. Instead, they were more likely to be interested in their own wealth and power. Because they needed supporters, they spread the wealth to important people who backed them. The common people, however, were not very important to the caudillos, so little of the wealth trickled down to them.
Caudillos typically came to power via military strength. They stayed in power through military strength and through the support of various local powers throughout their countries. They relied, then, on the support of the military and of powerful figures, not on the support of the masses. For this reason, the masses did not tend to benefit from caudillo rule, while the caudillos and their supporters did benefit.