I don't believe it's every generation. More like every three. Depression era grandparents have largely passed way, and taken much wisdom with them. Their parents rebelled against them--stupidly. Then they had kids, who now have kids. Those kids will be similar to depression era grandparents before it's all said and done. And so on.
As for the rest, the reason intellectuals hate capitalism is simple. It's rebellion against Nature. Capitalism is natural. Any deviation from capitalism is imposed on man in some form of tyranny, well-meaning or otherwise.
To me, the hippie/left culture is a rebellion against death, against Nature. They simply cannot accept life on its own terms--hence, they wage war against inequality, against war, against climate change. Look at the natural world. It is filled with violence, war, death, and cataclism. It's just the way it is. They think they can perfect life. They are wrong.
Also, they do it to get chicks. They can't do sports, they aren't good looking, or fun to be around, so they go for nerdy chicks by being intellectual radicals. It all boils down to the basics in the end.
Actually, if you look at voting history, the boomers voted GOP at a higher rate than the Depression/GI Generation. I can’t believe how many folks I meet who fall for LIBERAL Tom Brokaw’s “Greatest Generation” propaganda.
Actually, they do it to get guys.