For political writings, he's a knock out. If you want to know how a libertarianized society would handle some of the weirded out scenarios the detractors throw at them, his books expose the detractors hypocrisy and dishonesty almost flawlessly. His Henry Martin books are wonderful space opera. If you are looking for pure poetry however, stick to Shakespear, Chaucer, and Poe.
Only during the primaries.
BTW, my son is a Libertarian. I guess I raised him right. ;) As long as he's voting Libertarian in Texas, it shouldn't matter that much but he won't vote like that during a close political fight.
He married into a dem/green family. We took their daughter out shooting before they were married and she loved it.