RE: "I will pay for information if it will help me, but the examples I've given is basic information that's been written about for free so many hundreds of times"
I suspect your google-fu is stronger than most. Many people don't have the skills or time to do this. Should I spend 2 or 3 days searching and building a marketing strategy that works in 2012 by filtering through all the stuff written over the last 4 years and half of it is out of date or should I pay $99 dollars to get it in my inbox in PDF form. For many the $99 makes sense.
They are certainly not ripping off the startup community! If you even value your time as a startup founder at $100, it's cheaper just to by the dumb book.
Most startups doing subscriptions are doing b2b or b2h (business 2 hacker examples: github, seomoz, etc) business. Businesses and to a much lesser extent hacker don't care about the cost, but look at the value provided.
RE: "There seems to be no imagination in pricing, only to charge more and more. It's bad advice and I'll bet its mortally wounding a lot of young startups and impressionable kids..."
This is absolutely absurd! This is like saying "There seems to be no imagination in cars today, only to get better gas milage more and more". Of course, that's the point of a business is to charge so much your customers complain, but still pay you none the less. You're capturing the most value possible, while they still enjoy a net gain.
I'd argue even if this is bad advice for a majority of people, it's still good to get it out there that it is possible. Once we know it's possible, much like the 4 minute mile, we can achieve it. When it's locked away and only a choosen few know it is possible that is the real danger to impressionable kids.