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Well, as I said, I've finished the book, and just thought I'd make a few comments about it (consider this my personal review):
To get right to the meat of it, the title throws you off... because this book is not really about the Pirate's dilemma, it's about Rebellion Against Authority. The book examines various recent movements, primarily driven by young people, that observed the status quo, decided unilaterally that they did not like it, and set out to enact change. The movements Mason discusses largely did not enact change from the inside--that is, through gradual change as a part of the system--rather, these groups espoused violent change, preferring to blow the barriers up rather than circumvent them.
What Mason's book does not provide is how these recent examples of rebellion are really any different than those rebellions of decades or even centuries back, or why they are particularly significant now. In every case, Mason illustrates how that movement, however radical or ground-breaking it was at its start, inevitably became folded back into Capitalism As We Know It, lost its status as Revolutionary, and ended up being merely Evolutionary... at best, a medium-sized asteroid that diverted evolution into a new direction, but one that was still within its original design and processes.
Reading between the lines, we find the implied question to the title, the real Pirate's Dilemma: What does the Pirate do when they are no longer Pirates? The implied answer: They become Capitalists, just like the rest of us... or they fade into oblivion. Pirates don't remain pirates... sooner or later, they conform, give up, or get discarded.
For me, I was disappointed that the book concentrated on elements like punk and hip-hop, but on the subject of literature, said virtually nothing. In fact, as the book centers on Capitalism, it all but ignores the independent artists of the very movements it lionizes... it reduces them to producers, addresses their art as little more than widgets (while celebrating the fact that their actual quality was of no importance), and dismisses petty concerns like artists getting fairly compensated for their Pirated works in a single sentence:
"Artists not getting paid for their work is a problem."
Overall, I got little out of this book, other than: That the Youth Movement At-Large does what it does largely because it is too automatically dismissive of its elders to try to learn and work within existing systems; the suggestion that an artist's work, at root, has no real value; and that Capitalism Endures, no matter what nonsense you throw at it.
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