Some time ago, I bought a license for a font to put on my own book covers.
And I've been asked immediately: "Why don't you just use a free font?" There are gazillions out there. I even rummaged through hundreds of them, and ended up again with the one I like best. So I paid Juan Casco for his amazing work.
I have honestly no idea how much time it takes to make a good font. Days at least, if not weeks (I dare guess the latter). Though I know the theory down to microtypography, making fonts is not my line of work. I prefer to leave it to people to whom it is a work of love, for their fonts will be the best.
On most book covers I made so far I used free fonts, either because they were already in my huge collection of free fonts, or because authors had a certain font in mind. It is interesting that the less indie a project is, the more picky people are about not paying for a font. Please mind that not every publisher or games company makes a fuzz about this. My last employer didn't. Here's their reason: tell your artist to search for a free font in order to save 30 bucks, pay actually 50 for the time they waste searching.
For indie creators, I would understand the question whether they want to pay for a project that might not pay out. With companies, I don't get it. But there are surely reasons: Companies calculate with their budget for a project, and everything gnaws off that budget. The people doing the calculation see the immediate price, while the payment for the artist who searches for hours isn't obvious unless one has it on their mind.
Indie creators, who usually aren't rich anyways, ponder the value of other people's work. They might not be willing or able to pay, but they do pay by the time they search for a free font.
I could have done that too. But there's more to paying for a font: I wanted This. One. Font. And no other. I want to look upon my book covers and be happy about them, instead of having that tiny devil on my shoulder who whispers: "See, Scrooge, you could have had the one title font you wanted, but you were too stingy to pay for it."
I prefer that tiny devil to sing bawdy songs all day instead of mimicking remorse. If my book cover isn't worth 30 bucks to me, what's my own work worth to me? How can I expect people to appreciate my writing (and covers) when I don't appreciate the work of the font creator?
Please don't mistake me, I don't mean to blame anyone who uses free fonts. With the internet, art - including fonts - has become terribly cheap. A good deal of fonts is always part of text processing programs, pre-installed on devices, and it never crosses one's mind that these fonts have actually been already paid for. Then there are the countless free fonts on the web. Not that I would complain.
The downside is that this fuels the expectation of getting almost everything for free. But even these fonts have been paid for: the creators pay with their time and possibly with their webspace, hosts like big font sites pay by advertizing, and sometimes even track you in order to show personalized ads. Sounds evil? It's simply how you pay for the free stuff you get. (I might rant about the pay-with-data issue way more, yet other people already did this more proficiently than me.)
Finally, time for fun things. Or macabre. Depends on the point of view.