One thing is that traditionally users don't buy fonts. In the past, the only people you expected to get any money from were people who got paid to set the type. You might spend months to years working on a single typeface and in that time a considerable amount of work had to be done to market it (done usually by the foundry you were working with), because after that much time a real flop might mean the end. Over the last few decades the barriers for creating and distributing type have definitely shrunk significantly, but there's still an issue over how type should be licensed and exactly what it needs to compensate for. Many typefaces are created by people who are otherwise employed as graphic designers or illustrators, while the individuals who are solely type designers have to contend for their living with type only in what is now a sea of free or corporate subsidized fonts (i.e. what came on your system).
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If what I just typed makes no sense at all, I blame either my insomnia or the ambien which I refuse to take for it.
This is, I think, the real reason: if you're going to make a living selling fonts, you're going to be selling them to agencies and publications. There aren't enough of those to make a living if your fonts cost $5 a piece. There are a lot of things priced this way.
Obviously, the other issue is that a publication will pay a gigantic amount of money for a typeface, but HN readers will only reluctantly spend $21. Rather than trying to bridge the gap, it makes sense to sell to the party that values your work the most. Again, this is a very common and sensible pricing dynamic.
Sure, but you're going to have to give them some time, because they're only just now figuring out how to license web fonts in such a way that they're tied to sites or pageviews instead of granting blanket permission to use the fonts for websites, magazines, and investor reports.
In the meantime, you're not where their bread is buttered yet, so the urgency isn't there.
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If what I just typed makes no sense at all, I blame either my insomnia or the ambien which I refuse to take for it.