These crazy outdated licenses that let you print as many magazines or books you want forever, for a one-time price. But if your hobby is making apps, then suddenly the same font will cost you 50 times more - for a single year.
I guess these font sellers imagine there’s still some app boom - a Klondike rush with developers bathing in dollars. Maybe if their licenses were more realistic, piracy would be less of a problem.
I'd argue that complaining about font prices is less like a Hermes bag, and more like complaining about high-end ingredients when a supermarket has cheap stuff. Yes, you can get away with cheaper materials when cooking, but the final product will deeply suffer.
The "problem" with free typefaces isn't their quality, it's their ubiquity. Since everyone can use them, they are used everywhere. Licensing something less common can help your product stand out from the crowd.