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 it is probably right that they would find it more profitable to sell 100 copies for $10 than 1 copy for $1000. But I do wonder, it could be that the occasional $10,000 sale to a large company pays more in the long run for less hassle. It’s hard to know. Do any creative agencies release their sales information?
I’d say there should at least be a small niece for a company to profit off the back of less expensive more reasonably licensed font sales. I don’t know how many lawyers a small company would need to do this though. Would they be sued by Adobe (either for fonts that look similar, or with pointless lawsuits just to wear them out?)
I suspect they are printing more money with the 1-10 megacorps who can afford to pay millions of dollars for per-eyeballs licenses.