Readability tried something like this. Among the problems: authors / publishers didn't sign up, and money collected had to be distributed or reimbursed. Unclaimed funds eventually were awarded to a charity.
Though I believe Readability had good intent, they took a great deal of flack for this.
Most of the weirdness in the case of Readability came from charging their users before they had established the relationships to pass the funds along. Collecting funds for authors sort of advertises that you are paying them, doing it while not being able to pay them is pretty shady.
I guess a better way to bootstrap such a thing would be as part of some sort of time tracker, show the user where they spent their time at the end of the month and wire it up to a tip jar system.
I can see this being the management team getting out in front of itself though. I can understand how others would criticize. I don't see any obvious signs of intentional malfeasance. Perhaps poor judgement.
The solution they proposed is one that I've been thinking should be applied to online content for some time.
Though I believe Readability had good intent, they took a great deal of flack for this.
Money weirds things.