A rant on web font licenses

Depends if the font is $1200 or $20...

Oracle will sell you a perpetual license that you own forever.

Most foundries won't do that for fonts (at least for web).

This is the same line that made me scratch my head. I'm a non-network guy who has been stuck migrating our phone system from PRI to SIP, and every time I think I get it done, I have to buy another license from Cisco--that our resellers didn't tell us about at the beginning of the project. The latest issues is our voice gateways need a special security license to handle TLS. Outside that, cost per usage is one of the most common cost metrics I've seen--sure if its SaaS it seems directly related, but this is for on-prem licensing--I get the exact same application, only I'm licensed by how much I use it, like the authors font licensing complaint.

MyFonts' licensing system effectively took down our entire website recently.

We have a font licenced for some number of pageviews (250,000 or whatever), and they track that via an @import in the CSS they give you which points to a URL on a subdomain of myfonts.net. Except they changed their licensing mechanism, didn't tell their customers and broke the subdomain the @import was hitting. It didn't fail immediately, just kept trying to load for ages, and so rendering was blocked and our pages didn't load. That was pretty frustrating.

This situation is beginning to improve if you know where to look. There are several typeface designers who offer both low prices and reasonable licensing terms for their fonts; for instance, David Jonathan Ross (https://djr.com/) has a "Font of the Month Club" that gives you one font per month at $6/month; even without membership you can get previous club fonts for $24; and the licensing terms are plain english. Matthew Butterick's fonts cost more ($120 for a full typeface; mbtype.com) but have a very reasonable plain-English license.

That said, usage tiers (where you must pay more if your website gets a certain # of views/month) seem ubiquitous. I think these are ok - big websites can afford to pay more, and I wouldn't be surprised if a disproportionate amount of a typeface designer's income will come from a few heavy hitters; so without charging more for big websites, they'd have to raise the price for small ones, pricing hobbyists like me out of the market. Big font companies, though, often require you to install intrusive javascript tracking code to enforce these agreements, which is a step too far for me.

Fonts are pretty much a pure crystallization of the "information wants to be free"/"artists want to be paid" tradeoff. Digital fonts are nothing but information, so it seems absurd to charge more for using them on more websites/in more documents/with a larger team - there's no additional cost being incurred!; but without artificial restrictions on reuse, typeface designers wouldn't get paid at all.

tl;dr You're going to get better treatment and better prices from little one-person font designer shops than from the big companies (Monotype, Hoefler & Co). Unless you're a big co yourself, the OP is right; they're a waste of your time. But the little guys are a decent option, you just have to hunt around.