Obama isn't working out the details of some grand vision; he is doing what Machiavelli called "temporizing with accidents." He has specifically referred to FDR's principle of experimentation: try it, see if it works, and if it doesn't work then try something else.
When Oakeshott criticized rationalism, he wasn't advocating irrationalism, but instead a kind of empiricism, what he called "feeling for the balance of the thing." His "rationalists" - he was primarily thinking of Fabian socialists - imagine that they know a method of analysis that allows them to design major social changes in detail and impose them without much reference to facts on the ground or the opinions of others. Their "rationalism" is in fact dogmatism. That's the hubris against which Oakeshott warns. Could anything possibly be further from the Obama approach?
And that was my point.