So, focusing on fonts and types in particular:
I drifted a way from worrying about typefaces but for awhile was really focused on them for publication reasons.
Things have changed a lot in the last 10 years or so because of Google Fonts and other similar things but my impression has always been:
1. For whatever reason, there seems to be this black-and-white schema that font licenses either need to be ridiculously expensive and locked down, or completely free. I've never really understood why you couldn't go buy a personal use of a font (with generous use allowances) for say, 10 USD. The idea that people might actually be willing to pay if it were affordable seems lost, probably because it's usually large firms commissioning the typefaces to begin with. But if you make it for an initial project, reap the benefits, and can relicense it, why not do so understanding that you might make some money from large numbers of small purchases? (For what it's worth, I think similar issues arise in other areas where there's overly restrictive IP -- you get this black-and-white seesaw between draconian IP and totally libre offerings as a blacklash, with nothing in between).
2. What seems to evolved in some cases is some initial commission by a large firm, followed by libre licensing afterward, which makes some sense to me. Then the designer gets paid a large fee, people get to ooh and aah at the beautiful font, and the company gets extra advertising for commissioning a nice libre font. It's basically a form of advertising -- people download the font and see that company A paid for it, and then they get some branding association. The desire for fresh branding and individuating, along with goodwill, is part of what drives the commissions. Or put some relatively brief term on the commercial font, after which it becomes open.