The more complete it is with respect to specialized features like ligatures, old-style figures, international lettering, weight variations, display-sized variants, etc. etc. the more this compounds upon itself.
Just think about that before you use this to download Gotham/Proxima Nova/whatever cool font you want to use but don't feel like paying for.
The exact same can be said about programming, often multiplied tenfold by the number of engineers.
But the software industry has long understood the zero-cost of duplication, and counting on scale to build up massive revenue. Writing a good mobile game is heavily labor-intensive but you can sell it only for $4.99 if you do it a million times.
More specialised software costs more not necessarily because it's somehow more expensive to make but because the experts are willing to pay more because they receive more value out of the expert software. And usually there are cheaper options for small players who only need parts of the functionality. So the sellers understand that ideally you would only charge each customer as much as they're willing and able to spend because each time you would still charge something instead of being left without revenue at all.
There's revenue in market segments. A marketing studio can afford to pay $10k for a font for a $500k advertisement campaign. An application developer or a personal website owner could pay a onetime $20 for a specific font if he's a design enthusiast but wouldn't pay $100 and rather go with some open, free font. If font licenses cost too much they are not even on the radar for spending except in the high-end cases only. I've never considered buying a font myself but it might become an option with sufficient selection of fonts at a reasonable price.
Fonts have historically been expensive because each variant is a significant amount of work, and folks often want ALL THE VARIANTS. You're looking at years for a single variant, and a single family of fonts may be someone's life work. Yes it's non-trivial to create an italic version of a font. Kerning each weight... want fonts optimized for a given size (opticals)? That's a ton more work there too. Of course it costs money. Don't except that a license to redistribute that for a pittance — there's a big difference between a license to create documents that will use a subset of the font and embedding a whole font that your customers could then use for any purpose they see fit essentially bypassing any sort of income. Although I'd argue you'd be best off using system fonts in the vast majority of use cases lest you come off looking like that guy who uses Comic Sans everywhere.
That said, while legacy companies have been (and still are) reluctant to embrace newer technology, some are better than others. Most foundaries will let you preview fonts online and offer a wide array of samples to view. Typekit was a great resource where you could license fonts for web use. Of course Adobe bought and mangled the ever living hell out of them. In terms of foundaries, FontShop has been at the forefront of embracing technology (including all the cool things you can do with OpenType) and typically licenses for their excellent FontFont family of fonts are very reasonable. Monotype bought FontShop a few years back so we'll see how long that lasts though.
My take on it is that if I'm using something to make money I should pay for it. When I setup my letterhead and business cards I ended up buying licenses for the font variants at around $30-$40 per. It adds up, but it also gets you thinking about whether or not you really need the bold, condensed, italic variant or not.
Look -- I had a conversation last night with a friend of mine about the new Nikon mirrorless system. He was a pro photographer for a while. His comments? People don't buy photographs anymore so there's no sense in him investing in a new system. He let the lease run out on the studio this year and bought a boat instead. Here's the key difference between a photographer and a typographer: one finished photo may be the result of a few days or weeks of work[1], one font is going to be an order of magnitude more work.
1: Yes there are ALWAYS exceptions and outliers -- e.g. for the stuff I shoot I spend maybe a few hours in post per shot at the very most and that's pretty extreme for me.
> I am sure this system can be improved to benefit both font authors and font users
One approach that could work is draconian DRM but no one liked the drawbacks. You must have some idea on how improve the system, since you are so sure it can be improved. I'd suggest you implement this idea - you'll be doing everyone quite the favor and become rather wealthy as a result.
> Like to get a font to use in your app, you need to pay $5,000+ for any decent looking font.
There are many high quality open source fonts available. For example:
http://www.latofonts.com/lato-free-fonts/
Many foundries such as Grilli Type have free trials (https://www.grillitype.com/free_trials) and reasonable pricing for very high quality typefaces (https://www.grillitype.com/shops/gt-america <$1k for desktop + web)
And just so you know - app updates count as new installation in terms of font licensing. So in you example from GT America font, if you have an app that is installed on 5,000 phones (which is quite easily achievable on app store) you will have to pay $245,000 : https://cl.ly/21d48f64f529
And here is a mobile app licensing terms on fonts.com:
> LICENSES FOR MOBILE APPS A mobile app license permits the embedding of a font into the iOS, Android or Windows Phone mobile platforms for a single title and a set number of app installations. You can view and modify the installation limit from the cart. App installations can be spread out across the platforms your app is available for. A new license is not required to cover updates to an app, however installations of newer versions of your app do count toward your installation limit. Learn more about licenses for mobile apps
While every dev seems to fancy themselves a great designer, the reality is that apps end up looking like they were rejected from MySpace and Geocities for being too ugly. Custom widgets using non-system fonts (much like in the desktop and web sphere) often lose out on important accessibility baubles as well. I can certainly understand a desire for completely custom widgets on something like a full screen game. But to eschew the system fonts? Meh.
Meanwhile if your main use is branding you don't need to embed or subset the whole font. Include your logo or whatever as a sprite (vector or bitmap) and get a license for that sort of usage, it's cheaper.
If $50/seat is too much, the correct answer isn't "hey let's pirate it for my commercial app".
When did I say it was a correct answer?
It's led to larger tech companies rolling their own, which often means just taking something already out there and changing a few corners slightly and calling it a new work.
As others have mentioned, there are lots of high quality open source fonts too. For example, Adobe's Source San Pro, designed by Paul D. Hunt, is popular on many websites. It was designed for UIs and comes in a whole range of weights:
https://github.com/adobe-fonts/source-sans-pro
Another font designed for UI display is Clear Sans commissioned by Intel:
When looking for a font, the quality can vary widely, but the choice is enormous.