I was reading NR when it was a a weekly alternating with a newsletter and had my own subscription in 1964 which I kept until a year after WFB died. I could see even then that the fire was going out. WFB had his own weak spot, he reached the conclusion that the nation would be better served if private ownership were ended. That was jarring but every other part of the mag was very enlightening. I have had an ongoing sense of loss missing the humorous wordplay of his own writing.
I don't think so. Buckley had been fighting for private property and free enterprise for 50 years. In 2000 it seemed like the war had been won and there were no more battles to fight. The USSR was no more, and Clinton was saying that the era of big government was over. Conservatives, it seemed, wouldn't have the experience of being outsiders in a minority who won over the country or world. So Buckley said that if he were young and wanted the same life he would be a socialist. He wasn't saying that socialism was a good idea or that private property should be abolished. Think of him as a lonely old Indian fighter who misses the fight and realizes that he has more in common with the Indians that with what replaced them. He wasn't wishing that the Indians had won. He missed the fight and missed the world of his youth.