There are two definitions of rationality to keep in mind: epistemic rationality and instrumental rationality. An agent is epistemically rational to the extent it update their beliefs about the world based on the evidence and in accordance with probability theory - notably Bayes rule.
On the other hand, an agent is instrumentally rational to the extent it maximizes it's utility function (i.e. satisfies it's preferences).
There is no such thing as "rational preferences," though much ink has been spilled trying to argue for them. Clearly preferences can't be rational in an epistemic sense because, well, preferences aren't beliefs. Now can preferences be rational in the instrumental sense? Well, actually, yes but only in the sense that having a certain set of preferences may maximize the preferences you actually care about - not in the sense of some sort of categorical imperative. Suppose a rational agent has the ability to modify their own utility function (i.e. preferences) - maybe an AI that can rewrite its own source code. Would it do it? Well, only if it maximizes that agent's utility function. In other words, a rational agent will change its utility function if and only if it maximizes expected utility according to that same utility function - which is unlikely to happen under most normal circumstances.
As for Bob, presumably he's a human. Humans aren't rational, so all bets are off as far as what I said above. However, let's assume at least with respect to utility function changing behavior Bob is rational. Will he change his utility function? Again, only if he expects it to better help him maximize that same utility function. Now then, what do we make of him editing out his alcoholism? Isn't that a case of editing his utility function? Actually, it isn't - it's more of a constraint of the hardware that Bob is running on. There are a lots of programs running inside Bob's head (and yours), but only a subset are Bob. The difficult part is figuring out which parts of Bob's head are Bob and which aren't.
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I've just ordered a copy. It keeps coming up as a useful reference, even if it might not be exactly what I'm looking for. Thanks for bringing it up!
Having read, Influence, The Prince and, 48 laws of Power I found Cialdini's book the most satisfying to read because it was filled with empirical research. The latter books I mentioned were no doubt excellent reads however anecdotal. Also, Influence is presented in the least "dark arts" ways from the other two. The book is about learning to stay ahead of influence just as much as it is about influencing.