(this feels incomplete, but I am putting it up as an answer hoping it prompts comments or questions that further stimulate...)
I think there are stupid people, I don't think people are stupid. I also question the implication that people who choose to continue to live in the imiserated status quo are making stupid choices. I think it is short-sighted, demeaning, and ultimately not really helpful.
In my experience people make choices based on what seems like the available options and what will work out for them best. This is often clouded by morality, but I think that morality is actually pretty optional. As this relates to anarchists, I think that a lot of people make what is a pretty rational choice - that to continue with known variables, which to anarchists generally is read as compromise, collaboration, selling out, or apathy. I would view it more as resignation: Sure, it might suck (and some of it doesn't: look at this fancy car/house/tv/whatever!), and sure, in the long run it might not be in our (or our loved one's) best interest, but for as much as we live lives confused by concepts like linear time, we are still animals that live very much in the present- and short-term.
When I worked with homeless kids (not, mostly, anarchists), they frequently made choices that were inscrutably "stupid" to most people, but they were based on the realities of their lives as they were experiencing them. And given that the bottom line for a lot of them was survival today/tonight, they made extremely smart fucking decisions. Not all. Some made extremely stupid decisions, but for the most part, smart.
From this, I started to think about other folks I know who choose to live lives in compromise/service to 'the system' (yech). My parents aren't stupid. They ARE conflict averse, and they made choices based upon this and their concern for raising two children, one of whom remained a dependent (with their own dependents) well in to their thirties. For these two smart people there is a combination of psychological factors and environmental factors that have led them to be where they are today. Pretty much everyone makes compromises, and that isn't necessarily indicative of stupidity any more than it means that all compromises are equal or that anarchists should compromise their attacks and criticisms of 'the system' (yech).
Just because I understand why people make choices they do doesn't mean that I have to agree with them. Also, to refer back to my parents - I will never convince them of my perspective over the path they've chosen. Nor would I try to. My goal is not to win converts, or to add numbers to the A-team tally sheet.