But here's a partial response, focused strictly on the phenomenon of college education:
It would be easier to embrace academia if the inflation-adjusted cost of going to school were stable or decreasing, rather than growing at 6.8% per year between 1987 and 2009:
http://seekingalpha.com/article/144835-college-tuition-expla...
With a few exceptions -- gods bless MIT Open Courseware and the Khan Academy -- the academy does not scale, nor does it even try very hard. The Internet gets more inclusive every year. The academy does not. As economies grow around the world and the web gets built out, we add more and more people to our public discourse, and the percentage of those people who've gone to Harvard just gets smaller and smaller.
It would be easier to embrace academia if a young academic had more than a snowball's chance in hell of finding an academic job. Nostalgic baby boomers can look back at a time when new colleges were going up at a great rate and they were all hiring staff. Not so much anymore. I know lots and lots of people who would love to do laboratory research, for example... in a world where it didn't involve an enormous pay cut, enormous career risk, incredible devotion, high stress, difficult politics, and potentially the sacrifice of one's family life.
It would be easier to embrace academia if academic research, much of which is paid for with public funds, was published in open journals that all taxpayers could read for free, instead of in expensive private journals that only other academics can access for "free" via their university libraries.
And a lot more people would be touting the virtues of college degrees if the unemployment rate for college graduates weren't at its highest point since 1970:
http://www.usatoday.com/money/economy/employment/2010-12-06-...
It may not be entirely the intellectuals' fault that college education costs more than before and can take longer than ever to pay off [1], but you can't expect people not to complain about it.
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[1] AFAIK college education does pay off, handsomely, even now. Although if tuition keeps growing and wages do not, shouldn't we feel free to wonder, out loud, how much longer this can remain true? Isn't that what a numerate intellectual might wonder?