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The problem is one that crops up in writing fiction all the time. The difficultly lies in the fact that the pronoun "he" or "she" always has to refer back to the last person named.
In your quote:
"Bill was not the brightest of men, and in late night drunken monologues he would often relate bitterly to his son how in hindsight he could have perhaps chosen a better target."
Here, it is his son who could perhaps have chosen a better target, and that is the problem, because that isn't what you mean.
What you mean to say is:
"Bill was not the brightest of men, and in late night drunken monologues he would often relate bitterly to his son how in hindsight Bill could have perhaps chosen a better target."
Though this sounds awkward. A better option might be:
"Bill was not the brightest of men, and in late night drunken monologues he would often relate bitterly to his son how in hindsight a father could have perhaps chosen a better target."
I often find problems with pronouns and their referents when I read back through things I've written. Sometimes it doesn't matter too much -- if there is one clear point of view and you keep referring to that "he" or "she", then the reader will probably get you. But, generally speaking, a pronoun refers back to the last person of that gender named.
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