I was really fascinated by the reaction kicked up by a cultural writer attempting to write an article about a relatively famous libertarian philosopher (Nozick, and to another extent Hayek).
To put it mildly, the reaction among even some liberal or conservative writers/economists has been "what?". Or something along the lines of "this guy doesn't know what he's talking about". It came down eventually to something like a Turing Test for ideology. If you can explain the opposing views from their perspective to the point of being able to appear like one of them, that makes your rejection of such views more plausible and complete. Because you clearly would be able to understand such views but still find them ridiculous. The association with Mill's defence of free speech on these grounds is not by accident. Mill effectively says that if there is no substantial opposition to a view then we should find opposition and arm it with the strongest arguments available before we can safely conclude there shouldn't need to be opposition to such a view, and that for this among other reasons, we need absolute protections of free speech in a free society. There are lots of public positions which have shifted over time (drug legalisation or homosexuals and marriage laws for instance) in part because these views were permitted to be expressed, questions asked, and the strongest available arguments were aired against the strongest arguments available in defence of the status quo. And it is the status quo that is being found wanting and is abandoned.
The real effective problem is that most people take very little time to try to understand the strongest arguments of their political or ideological oppositions. People in relatively obscure political movements (like libertarians) have plenty of time to try to understand the mainstream positions on anything and everything. It's all around you in those circumstances. So understanding the straw men, the weakest arguments, the populist movements, and even up into the academic defences with their boring technical treatises and complex mathematical equations comes pretty naturally when you're surrounded on all sides by people who breathe in and out and the same things get spouted out of their mouths. Outside of academic circles, libertarianism as a philosophy isn't extremely popular (it isn't very popular there either, but its general view toward public policy positions are more so there than among the general public). Although some "normal" people claim to be such but when questioned about it, they either don't know what it is (usually some vague associations with it being "not-communist/socialist" will come up) or adhere strongly to some very curious political positions that appear wholly incompatible with almost any version of libertarian political philosophy from pragmatic utilitarianism to the anarcho-capitalistic sentiments of Ayn Rand. Ie, they're actually conservatives who heard a fun word for something like "get government off my back" and ignored the part about "and everyone else's too".
Similar problems emerge in other areas of thought. It's pretty clear that atheists are not well understood. Whereas Christianity is rather well understood by minor factions both related or unrelated within American society. Mormons, Jews and atheists all score very highly on general knowledge of religion or religious dogma of any kind, including Christianity, and much higher on non-Christian views than Christians do on say, those "filthy" Muslims or Hindus, much less Jews, Mormons or atheists, all much less common than Islam or Hindu worship globally speaking. I view this as certainly related to the general level of education possessed by the average atheist/secularist (true as well for Mormons and Jews). But it's also obvious that being part of an obscure minority tends to give a very different amount of perspective relating to the more popular positions held by most people, and a lot of time and attention to pay to such things, examine them, twist them around, and still end up rejecting them.
That is to say: that most people believe a lot of bullshit (not just their religious beliefs, not by a mile) and don't bother to defend it or consider it very carefully at all. The reason these arguments on things like free trade or anti-technological biases or concerns about inflation keep coming back up again and again is that most people have a set of beliefs... and those beliefs don't match the reasonable conclusions drawn from evidence nor the reasonable intuitions that would be predictable from even mainstream economic theories (much less some more radical libertarian ones). You end up having to explain opportunity costs and fixed costs as a hedge against inflation to people buying houses because there's this psychology surrounding debt, even financial debt incurred in a housing expense that can be offset by inflation and unreasonably large tax deductions, that demands that we feel we get rid of it. You end up having to explain that the pot of goods for most of us includes more than just the everyday prices on gasoline and milk that we can see readily moving up and down and also includes purchases that we may make every couple of years, or if we're very fortunate couple of decades, on appliances, automobiles, televisions, and computer parts (and even houses) and that this matters for inflation too. And so on down the line into minimum wage laws, rent controls, trade restrictions, rent seeking public policies, regulatory capture and so on.
It's a mad world out there and most people have never studied it. So to expect them to understand the parts they don't know anything about would be a little silly. But to expect them to write articles about it as though their thoughts warrant consideration, we should expect them to have done a little research. Enough that they know not just the flimsy material that the average person flings around regarding an obscure subject (like libertarians and atheists) but they can be armed with the strongest arguments and explain or examine them. Maybe they will still reject them in favor of their own.
But they should at least attempt to understand by speaking in the voice of their enemies and opponents on these ideological fault lines. And not by casting such views in the most unflattering lights (real or imagined) in order to dismiss them.