This is great feedback for typographers. Font Spring's[1] license is pretty nice. I just finished the first draft of license[2] for the upcoming Berkeley Mono typeface. Basically, we want people to enjoy using the typeface with zero worries. Our license is very generous (See §2. in [2]) - all uses allowed whether it is personal (non-commercial) or commercial license. We don't care if it is used in avionics, etched on nuclear power plant control panels or used to build your next operating system. eBooks, apps, servers, datacenters, whatever...with Personal license, you can do anything that is not deemed as commercial or business activity with explicit exceptions of professional use when working for your employer. With commercial license, you can do anything except modify the typeface. Absolutely no tracking, no webviews, no urls, no logomark restrictions, no app-install counts. I also understand why folks like Lineto[3] have so many restrictions - they're a big foundry and have big clients, but they should make provisions for smaller clients.

[1] https://www.fontspring.com/

[2] PDF - https://neil.computer/files/berkeley-graphics-personal-licen...

[3] https://lineto.com/information/help/licence-user-rights/lice...

Font licensing is annoying even for people in the industry itself – sadly a lot of it has to do with piracy and others who purposefully buy cheaper licences. Though my advice is to just look further, you won't see Monotype change their licensing model any time soon, but foundries like ABC Dinamo have made significant changes (like only taking company size into account, not users or pageviews) that others have started to adopt.

Swiss Typefaces (https://www.swisstypefaces.com) have some lovely fonts with a clean upfront licencing system that allows use on 10 workstations (aka designers) included in the default price.

Maybe look here: https://pimpmytype.com/category/fontfriday/

Prices and conditions on the few I checked seemed to be (relatively) sane to me.