Let me know what you come up with, there are likely some crafty solutions.
UBI may not solve this entirely but if it can free people of the need to worry about their economics whilst simultaneously allowing people to do whatever they want, for a lot of folks that is enough.
Additionally, I don't really see the issue with selling (NOT licensing) something up-front, if there is a culture of setting pricing to be reasonable and fair instead of the current leave-no-money-on-the-table approach.
Those that want to earn above and beyond can still find employment in critical services...banking, healthcare, government, whatever, while those that want to opt out of employment are free to do so on their terms.
So you don't have be in the market for a font to support fontmakers (or anything else).
On the other hand, the need to be able to sell things means the quality has to meet the customer's expectations.
For example, cars produced by free market companies far exceed in quality those produced by socialist operations.
In fact, I suspect you'd be hard pressed to find any examples of anything people made purely for their own amusement being better quality than items they made for sale.
For example, the software I write for my own personal use tends to be pretty slipshod, as it only has to work for my use case. I don't bother with coherent error messages, documentation, a decent user interface, or fixing any bugs that don't directly impede what I use it for. Doing that stuff is simply not worth my time unless I'm planning on distributing it.
So, a product for which people are willing to give you money in exchange. People are not likely going to buy a shitty product unless the situation involves monopoly (natural or otherwise) or regulatory capture
It's also possible to create content that's more experimental and creative, by focusing on more niche audiences. This is evidenced by the current golden age of TV and streaming, with a wide variety of dramas, comedies, documentaries, etc.
No, it does not. The need to earn money incentivizes people to work on things that allow them to extract money from others. This sometimes happens to line up with "useful", and there's probably even a positive correlation overall, but they're not remotely the same thing.
You're talking about things like acquiring money through force or fraud. This is not how free markets work. Free markets work by creating products that people want to buy and freely trade their money for.
If I create a widget and you want it more than the money it costs, I am not "extracting" the money from you.
I drifted a way from worrying about typefaces but for awhile was really focused on them for publication reasons.
Things have changed a lot in the last 10 years or so because of Google Fonts and other similar things but my impression has always been:
1. For whatever reason, there seems to be this black-and-white schema that font licenses either need to be ridiculously expensive and locked down, or completely free. I've never really understood why you couldn't go buy a personal use of a font (with generous use allowances) for say, 10 USD. The idea that people might actually be willing to pay if it were affordable seems lost, probably because it's usually large firms commissioning the typefaces to begin with. But if you make it for an initial project, reap the benefits, and can relicense it, why not do so understanding that you might make some money from large numbers of small purchases? (For what it's worth, I think similar issues arise in other areas where there's overly restrictive IP -- you get this black-and-white seesaw between draconian IP and totally libre offerings as a blacklash, with nothing in between).
2. What seems to evolved in some cases is some initial commission by a large firm, followed by libre licensing afterward, which makes some sense to me. Then the designer gets paid a large fee, people get to ooh and aah at the beautiful font, and the company gets extra advertising for commissioning a nice libre font. It's basically a form of advertising -- people download the font and see that company A paid for it, and then they get some branding association. The desire for fresh branding and individuating, along with goodwill, is part of what drives the commissions. Or put some relatively brief term on the commercial font, after which it becomes open.
Fewer commercial incentives may improve what bubbles up as the incentive process is sometimes interfering badly with the discovery, or production, of the best stuff.