Comment by rglover
I would happily pay for any font if I could get individual weights for say $5-$10 and entire families for $20-100 with any usage I want (print, web, etc). I feel like font foundries would print money this way. But for most projects, $300+ for a nice family (that can only be used in a hyper-specific context) is just insane when many free or cheaper alternatives exist.
Used to waste time and money with foundry stuff until Google Fonts caught up. Now I typically source something from there unless it's essential to the design.
I suspect they are printing more money with the 1-10 megacorps who can afford to pay millions of dollars for per-eyeballs licenses.