And I am glad you mentioned Oakeshott who hasn't been listed on this thread yet. I have just read bits and pieces, perhaps for the thread you can add an item of two of his you recommend for the freeper wanting to get a taste of his fine mind. (Again, as you have the time.)
Today, I will add to the list:
Property and Freedom by Richard Pipes (ISBN 0-375-70447-7) It was given good marks by everyone from National Review, the Washington Times and The American Spectator on one side to Literary Review and The New York Times Review of Books on the other.Pipes is a real Russian history scholar and contrasts how Property rights and law have developed in the west to how they developed in Russia and elsewhere to make his points on how Freedom is so closely tied.
Last night I was very happy with my recent purchase from Barnes & Noble: Dover's edition of Heath's Euclid (paperback, 3 vol. $10 each) You have to like it because it gives the axioms (A point is that which has no part; A line is a breadthless length) in Greek! (link for Bodleian MS pic) Shmeion estin, ou meroV ouqen. And then commentary on the Greek replete with references to Plato and Aristotle. Somehow that cigar had come to life last night.
Today its Jaspers on Kant. Jaspers is very readable and this edition is only $9.