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We're successfully using n2pdf to create pdf's from entire help databases. The product features a powerful scripting interface that lets you automate creating a table of content and index in the pdf. I don't know if other products can do that today. At the time we evaluated (admittedly, that was ca. 5 years ago), n2pdf was the only one.
Feedback response number JSAK99VC4S created by ~Chris Frofootherobu on 07/23/2013