It's really curious that in terms of energy spent on a problem, the site seemingly ranks feedback regarding price & price complaints higher in annoyance than freeloaders who pay nothing & say nothing. Feedback about pricing is also categorized under excuses, and boiled down to a simple set.

The boiling down builds on the implication that the author is happier if you are a freeloader than a feedback-giver, especially if your feedback meets the condition that you aren't yet comfortable paying.

This is also just as true if you are trying to give the author any amount of money, as long as it's less than $40 and you aren't a student.

So, you could be fully employed but living on a strict budget so you can move out of an unhealthy living situation, and decide that the book was worth your time to read but that you don't have the money, and then discover that the author thinks of you as "bro" and boils your exceptions down to "I already heard it." And that's just one example.

If you have questions about why you should pay, you will have to exert more energy than a freeloader (in time spent reading/parsing/contacting the author about your proposal that's higher than $5).

This is a problem. Sure, the book being free is "generous," especially if you're a freeloader, but the book is also very not free and the author makes this clear to the reader. Readers are considered to be reading under tacit subjective agreement governed by the author's published pricing frameworks.

The author (I don't know them, nor have I read the book) also seems rooted to the concept of intrinsic value. A lot of people in programming are not, and find it not only foreign, but a highly subjective, awkward way to request a judgement of others. Some people are really bad at deciding what is "worth" their time and many people do not actually think of their time in this way. Many of those same people also really want to support their community with what amounts to boundless creativity, if they can.

Like a lot of people who use the phrase "vote with your wallet," the author ends up redirecting a lot of the purchasing conversation to an either-or dichotomy: Worth it, not worth it. However in reading the details, it's clear that the author is also aware of a number of different ways of looking at the value of the book, but those ways aren't directly involved in the pricing mechanic. This reads strangely and creates an unnecessarily awkward hand-wave effect.

Racket is presumably a very nuanced language. I wonder if the book's audience is really comfortable with such a binary treatment of the customer & payment mechanic.

I think a really good start in repackaging this situation, as an author, would be to first determine exactly how much you need to make to keep the book alive. Especially if the book is in danger of not surviving/living on. What does it mean to you, in terms of expense, to keep the book alive? What is the minimum you'd accept yearly, for example? This is probably a huge point of leverage in communicating with the readers.

An exact number is important, because it's pretty unfair and inconsiderate to ask that the book's best audience blindly subscribe to a potentially limitless concept of paying the high end of the spectrum for works that are also free-to-most, in order to keep a book "alive". Especially if it's also fair to say that the book is of potentially infinite worth to the author, because this does not also reflect the reality of a single book in the market in isolation and could really muddy the emotional waters of charging money for something for which one could never be paid enough, if being honest in one's own intrinsic-value view.

Even if you think it can never be reached, publish the number. Update it as you make money and update the pricing model as things get better.

This would be much more fair to those who like the book, but who also grasp the inequity of the situation as it stands.