There is a always a level of pragmatism that strives to ease migrations between software, including entire operating systems, but the process tends to blur the gap between Free software and proprietary software. Consider the fact that companies that sell GNU/Linux desktops are struggling to please each and every customer and supplier (developer). If the freedom of software and hardware is preserved, this often means that the customer must then cope with a steeper learning curve. There are usually those who would bluntly accuse the company of betraying or exploiting Free software developers if proprietary 'shims' are included to remove adoption obstacles such as DVD playback and proprietary codecs.
Lastly, there is the perception that good products are advertised heavily. Wealthier companies, whose business model thrives in high cashflow (higher spending and higher revenue), are able to raise awareness of their products. The public is drawn in by hype and there is no equally effective response from the Free software world. Broadly speaking, advertising may be the Achilles Heel of Free software.
Possible solution: Education is probably the key to resolving the issues above. When stressing the value of freedom (and gradual loss thereof) users will be led to exploring more options. Not so many people are aware of real choice.
By raising the importance of user's control in computing and by understanding that advertising does not necessarily reflect on the quality of advertised products, people can better appreciate Free software alternatives to what they currently use. Manufacturers of software and hardware need to understand this as well in order for them to properly support lesser-known operating systems such as FreeBSD and GNU/Linux.
Pragmatism can sometimes be seen as a case of giving up because there isn't sufficient understanding out there. Hardware companies, for example, are sometimes unwilling to offer documentation that is needed for improved interaction with Free software. Their attitude is incompatible with Free software ideals simply because they fail to understand the economic benefits of customer-centric computing. Myths and fallacies play a significant role here.
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The great divide between developers and everybody else is so infamous that it created the "nerd" stereotype, but there is another divide which involves just developers. This problem is broad, but let us consider one individual example that is representative of most.
The problem: The creator of Linux, Linus Torvalds, considers himself to be pragmatic. He happily buys Apple hardware on which he immediately installs his own software and he takes pride in focusing on just the technical merits of his work. He rarely gets distracted by some of the more philosophical and seemingly boring questions that are associated with software. And that's a good thing, not a problem.
Torvalds distanced himself somewhat from the Free Software Foundation when he made the decision to stick with an older software license of theirs, the GNU GPLv2 (General Public License version 2). The main factor that led Torvalds to this decision is a set of clauses that forbids Tivoization. The term Tivoization is used to refer to a GPLv2 workaround that permits manufacturers to forbid modification joined by execution of a program. Some view this as controversial, but some do not. While Tivoization is legally permitted based on the GPLv2, this does not sit right with the spirit of the GNU project as a whole. The GPLv3 (version 3) was introduced to close the Tivoization loophole.
Torvalds has openly said that he likes Tivoization. He insists that Linux does not require some of the changes introduced in GPLv3. This led to mild hostilities and disagreements. By no means was this a case of infighting, but tensions rose and a little fracture appeared.
Possible solution: While the problem at hand is truly a matter of opinions, divergence in terms of ideologies can be endemic in the sense that it can lead to forks. It is hard to tell whether a solution is near, but it seems to be approaching. A year ago Sun Microsystems said that it would license OpenSolaris under the CDDL and the GPLv3 (dual). Past correspondence in the Linux mailing lists seems to suggest that Linux may have no choice but to swallow the GPLv3 along with terms that are perceived as undesirable by Torvalds. Alan Cox, unlike Linus Torvalds, has shown little or no opposition to this and he is very influential.
The greatest enemy to the success of Free software is Free software itself, as well as public perception. Some mild disagreements regarding the definition and values of Free software can lead to fragmentation, but there are usually some resolutions within sight.
What remains to be achieved is a grand goal related to education. Some computer professionals still fear what is yet to be understood a little better. Getting the word out is probably the best route to removing that last major obstacle.