Why are fonts so expensive? Why are there so many free fonts available? Who makes them and why? Gwern atempts to explain in https://www.gwern.net/Fonts  "Fonts are a rare highlight in software design—stable, with well-defined uses, highly-compatible software stacks, and long-lived. Unsurprisingly, a back-catalogue of tens or hundreds of thousands of digital fonts out there, many nigh-indistinguishable from the next in both form and function.

Why, then do they all cost so much, and who is paying for them all, and even going around commissioning more fonts?

The casualness of the highly marked-up prices & the language around commissioned fonts strongly points to designers spending client money, largely for the sake of novelty & boredom, functioning as a cross-subsidy from large corporations to the art of typography. The surplus of fonts then benefits everyone else—as long as they can sort through all the choices!"