These crazy outdated licenses that let you print as many magazines or books you want forever, for a one-time price.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.
You can try to create a Veblen good out of a digital artifact and play the all or nothing game, but it's proven very hard to restrict something which can be copied at no cost and with no limitations.
When you buy expensive clothes, it would be silly for the seller to try and license them to be only worn on Mondays, or at dress-code events, or based on your taxable income. People are not going to take your "license" seriously, even if you'd have some legal grounds and might well win a legal argument.
I have a great deal of admiration for artists and designers, and I know that creating a multiple-variant typeface with great applicability that's either historically correct or truly innovative is an art form.
This reminds me of Napster-era debates about artists' rights versus distribution.
That's why the usual approach, especially in this industry, is to not give people choice in the first place - this is achieved by renting, instead of selling.
Clothes as a Service is already a thing. A CaaS with excessively specific restriction of use? Might not be - yet. No doubt someone will try it.