This is a really, really broad question, so I'd recommend reading Tulio Halperin's book The Contemporary History of Latin America (which goes from independence until the 1980's) for a good comparitive history that deals with issues like caudillismo.

Caudillismo is largely a mixed bag, so it is impossible to say if on the whole it was good or bad. It is also difficult to assess the results of the rules of many caudillos, even if their influence was supposed to be positive overall, because many were systematically vilified in the decades that followed their rule and lives.

I've heard historians use Dr. Francia, dictator of Paraguay, as a positive example. He cared little for property rights and the comfort of the traditional landed elites, spurring a series of reforms (under his autocratic rule) which would be consolidated by his successors into a very successful, and largely independent, national economy. That is, until the War of the Triple Alliance united Argentina, Uruguay and Brazil against Paraguay (with the British urging them on and giving loans) until this independent experiment was ground into one of the poorest countries in the Americas, with many of its men dead and its industry in ruins.

I'd choose Antonio López de Santa Anna as an example of a negative dictatorship. He was a rather self obsessed figure who seemed to have sought not a single program to better his country so much as a narcissistic need for praise and acclaim. He is a complex figure though, sometimes vain and insipid beyond belief, like when he had his leg buried with full military honors, but also brave and sometimes doing things worthy of respect, like defending his country against foreign invasion (though because of his personality type the good he did may have been brought on more from a desire for fame than any more noble cause).

Caudillos tended to be forces for ill, but through absolute power they could also get things done that the traditional system couldn't. For example, only a caudillo with the army at his back could find the strength to refuse the many established landed or commercial interests. Caudillos could also stand up to foreign powers, if they really wanted to.