@vertigo Yes, absolutely. I agree with both positions at once. I just like the provocative way she asked the question.
With a product, you know that paying for the product will provide an incentive to provide more of the product, because the payment is conditional on the delivery of the product. With a charity you don't receive anything back directly, and it's difficult to know if you are getting your money's worth.
Paying for free software is difficult to describe as either charity or a straight purchase of a product.
I think there's a scale from where there's one principal author of a piece of software and you're paying them, and when there's a big non-profit and a big project and you're paying them.
In the first case I know that my money is providing an incentive to work on the software, unless they're already receiving a lot of money, are already working full time and another dollar won't help them prioritize their time differently. But anyway, I don't care much if they're buying beer or making property investments, as long as it's what they want to do and making the software and getting my money enables them to do it.
If the person keeps doing what can be observed to seem like full-time development, the money is probably doing good. If the person stops developing, you can stop paying (simplified).
In the second case it's less obvious that the money is going to sustain product development, it depends a lot on the organization as you say. It's also difficult to see if the organization's output seems to be the equivalent of twelve full-time developers or eleven.
A case close to this space is #mastodon, which has gone beyond feeding one developer and he is now paying others to do project work. Not a single developer, not an organized structure, somewhere in between. Is donating going to Mastodon development going to help make more and better code? I can't say for sure without looking at the sheets and the concrete results.
On the other hand, as Alanna is saying, if the software is providing you value to the clock of thousands of dollars per year, is paying a few dozen of dollars a year really something you need to follow up on and optimize? Every payer trying to audit their recipients is a lot of work that is also costing money. You're getting that value, can't you trust the provider to do whatever they think is best with the money you're paying in return?