Can game design be applied philosophy? I think so. Some people might say everything is applied philosophy, but usually unconsciously; I will leave that topic for another occasion.
Michael Oakeshott understood modernity as a response to the dissolution of communal ties that existed in the medieval era. In times past, people understood themselves primarily in accordance with their status, and the rights and obligations that derived from it. This made their self-understanding relational, and comparatively fixed. In modernity, by contrast, people became free, whether they liked it or not, and now had to confront the world as individuals. You are not who you are because of a status deriving from birth or marriage - you are what you make of yourself.
This makes freedom a challenge. Some people relish this prospect, and use the opportunity to pursue their life as an adventure. Others see it as a burden, full of unwanted risk and anxiety, and seek to avoid freedom where they can. The former are the stuff of classical liberalism (what a post-structuralist would call 'the liberal subject'); the latter are vulnerable to exploitation by authoritarians, who are willing to exert choices and make decisions on their behalf.
This was a common concern among 20th century philosophers who had witnessed first hand the rise of authoritarianism in the interwar period. The thinkers of the Frankfurt School - Fromm, Horkheimer, Marcuse - would very much have agreed with Oakeshott's assessment. Something about the conditions of postindustrial modernity produced in a large section of the population (perhaps even the majority of the population) a deep sense of alienation, powerlessness and unease, and it was this that led them to put their faith in the hypertrophied State. The 'fear of freedom', as Fromm called it, drove the masses into the arms of totalitarianism: better that than suffer the psychic angst of having to make decisions for oneself and deal with the consequences.
This bleak vision is tempered by William Galston's notion that education can inculcate in people the kind of character traits that will equip them for life in a liberal society. If they do not inherit the virtues of self-reliance, prudence, civility, and cooperativeness from their parents and communities, they can be taught them. This is what a liberal education is ultimately all about - shaping future generations into responsible actors who will respond to freedom in the appropriate way, and will be able to take advantage of its opportunities without fear (or descent into license).
In other words, while there are probably people who are predisposed, due to innate character traits or circumstance, to 'fear freedom', there is no reason why this should fate us to some kind of totalitarian impulse. And, in any case, the truth is that we probably all have our moments in which freedom appears to us as a burden that we would rather not carry: think, for example, of the last time you agonised over having to make a decision (say, whether or not to buy a house, or change jobs). In your heart of hearts, did you at that time never have the feeling of longing for a benevolent dictator to come along and make the decision for you? Would that not have struck you as a blessed release from the torment of being unable to decide? Ultimately, you would probably have recognised that there is something more authentic, more valuable, in making such decisions for yourself and living with the consequences, and there would have been something dehumanising about having the choice made for you. But one can recognise the impulse in oneself to seek to avoid the tyranny of options - what Kundera was meant by 'the unbearable lightness of being'.
So what does this have to do with role playing games? The superiority of sandbox-type play to the railroaded adventure path is, I think, found in its recognition that there is something more authentic about both DM and players exercising freedom - to arrange things as desired, and to pursue options within a broad scope of possibility, respectively. It is often more attractive to rely on pre-written, pre-plotted, published 'adventures', particularly when the alternative is the wearisome task of having to sit there with a blank piece of paper and pencil and think for oneself. At such times, the benevolent dictator of Paizo or WotC can have his appeal. But going down that road also somehow diminishes us.
This also suggests, I think, that the most worthwhile RPG products are the ones that educate - that provide the reader with the tools to run a sandbox game. It is the Kevin Crawfords of this world who are giving us what we truly need, and which will encourage in us the embrace, rather than the fear, of gaming freedom.