Ken Starks of Reglue recently published a thought-provoking entry on his blog, The Blog of Helios, suggesting that the barrier to Free Software adoption is bad documentation. He asserts that the lack of quality documentation is due to a philosophical approach to documentation writing, within the community, that he calls "good enough." By this, he appears to mean that document authors are writing to an audience similar to themselves, ie. people who are very experienced and grok most of what is being written.
While the problem he describes is common practice and it is a problem for the adoption of free software by newbies, it is not the main barrier to the propagation of GNU/Linux. Although good documentation is important, the main reason GNU isn't more popular is lack of OEM support.
The bulk of (perhaps all?) personal computers, sold around the world, are made by Chinese manufacturers. These OEMs supply MS Windows by default on their machines. They make it extremely difficult for distributors, like Dell, HP, Lenovo, et. al., to sell machines with any other operating system installed. They even go so far as to offer Windows for free, in order to ensure that it is installed on the machine. UEFI and Secure Boot will only magnify this problem. Cathy Malmrose (CEO of distributor, ZaReason) talks about these issues, and more, in her keynote at the latest GUADEC. Why they do this is anyone's guess, but collusion with MicroSoft (a possible violation of US Antitrust law) has to be considered.
What can the Free Software community do to change this? I'm not sure, it seems an intractable problem, but I'd love to hear what you have to say. Please give me your opinions in the comment section, below.