My dear Efraim,
Reading Oakeshott's book (unlike Kafka's) is what can be called a pleasure, and the more I look into it (after having briefly put myself through 'On Human Conduct' and 'Experience and Its Modes') the more interesting I find it. In fact I think the comparison between Arendt and Oakeshott couldn't be any more timely, as Canovan's interpretation starts to wane away, in particular because regardless of the canonical status of her book on Arendt she's a social scientist in the empirical meaning of the word and fails to account for both Arendt and Oakeshott beyond the space of the immanence of political theory and this is therefore entirely unphilosophical.
There're many things in common between Arendt and Oakeshott, what I particularly dislike is that Oakeshott, not unlike the other great theoreticians (Rawls, MacIntyre, Habermas, Benhabib) doesn't address too much the 'concept of the political', namely the foundations of political science and politics itself. Somehow I start to feel that he remains a political philosopher while Arendt is a philosopher of the political and with all the failing it involves, this is perhaps her greatest contribution to 20th century political philosophy. Nonetheless I'd shift the balance of importance from people like Schmitt and Habermas to enthrone Arendt and Oakeshott as perhaps the most important (and best) political philosophers of the past century. I entirely disagree with the idea that nothing 'really serious' can happen in politics, and Arendt has this experience and therefore projects endless reflections on the nature of freedom and action, on the concepts of the unlimited and limited in both. She shows the contingencies of political life in a way unknown before her and of course unrecognized by the tradition.
But in favour of Oakeshott I can say that no matter how much I don't pretty much accept his dealing with the social question he's not left it out of politics and this is where Arendt has the greatest failures, and this is a Heideggerian failure. Oakeshott is also much easier to follow, because I guess that coming from British Idealism he's rather epistemological, while Arendt as an existentialist is only concerned with ontologies. All her concepts are ontologically rooted, not in the meaning of Wolff's ontology (which is really the last stage of metaphysics in between Leibniz and Kant) but in the meaning of Heidegger... the ontology that follows the demise of realist phenomenology to be replaced by existential phenomenology. Arendt is a great philosophical essayist of the political and Oakeshott a great political philosopher. Their ideas on education are not as far as one would like to believe but I follow Arendt because she does root them on ontological experience and not in any pragmatic considerations, that as Arendt shows, are as contingent as the use of truth in the public space.
Arendt's theorizing because of its narrative character and its axiological but fragmentary nature is not a working model of politics but remains a paradigm of Modernity, while Oakeshott's model seems to me a lot more concerned with 'praxis' without forgetting its philosophical quality and the necessity of it expressed in his writings on education. This undoubtedly should be included in my work as one the central topics and no doubt this has barely been explored before. Heller argues that Oakeshott does not delimit enough the nature of politics in his theorizing (to the same extent that Rawls is concerned with justice, Habermas with formal ethics and MacIntyre with social organization, but not with the question of politics!) whereas Arendt does, and I tend to agree... but at the same time my disagreements with Heller at many junctures (especially in regard to ethics) are so outstanding that this demands a whole reconsideration of the whole issue. Certainly Oakeshott does not appear to me as either conservative or liberal or a maverick in any way, and in this he shares an undeniable ground of expression with Arendt that paves the way to the natural course of Modernity so terribly perverted by people like Habermas.