The problem with Stallman's approach is the assumption that most people want the free software ideal. The reality is that most people are not even knowledgeable enough about their computers to even understand what free software is all about, why it matters, and why they should care.
I would imagine that this is why he regularly makes a very vocal big stink about it. Just think: sixty-odd years ago, most people didn't know what a carcinogen was, why it was bad, or that it could be found in ordinary, presumed-to-be-harmless things like lead paint and cigarette smoke. Now of course, people who knew could always go, "Nobody cares about this! People die every day! Don't interrupt people's lives with this scary, annoying information!" Historically speaking, though, I'd wager quite a few people are glad people bothered to speak up and do something about it.
Most people do not care about the legal or technical issues surrounding their software, they just want to get online and do stuff. Stallman insists that when somebody sends you a .doc file, you should refuse to open it and insist that they send you a PDF or ODT file instead. Great when you are dealing with engineers and programmers, but not so great when you are dealing with people who think you need to create a .doc file in order to attach an image to an email.
I doubt many people gave a damn about things like anti-virus software on their Windows machines when the internet started to get popular with the masses. Somehow over time, though, a fair number of these laypeople wound up learning (likely a combination of the hard way and word-of-mouth) that they're probably a decent idea. Sure, lots don't know how they work, or where those little bits of nastiness came from, or that most such problems could be avoided by other means, but they know they're important and do bother with them, slightly.
Really, I get what you're saying, but there's a point where it goes from "not everyone wants to know how the car goes" to "people can't and won't ever change a flat!" Give some people potentially useful information and it *does* stand a chance of getting filed and used somewhere someday.