> I doubt that a programmer who wouldn't spend $100 for a font would spend $5
This is where we disagree then. I think there is a big psychological difference for most consumers, including devs, between spending $5 and $100. Even if you can afford both, the former falls into the range of impulse purchases, like getting a sandwich or a cup of coffee, where you spend without really thinking.
On the other hand, I think a $100 price is far more likely to trigger a more analytical and skeptical response. Do I really need it? Is it worth it? Should I research alternatives? Maybe, I should think about it and decide tomorrow... Etc. And the consequence will be a huge drop in sales.
Also, I also do think there are significant differences in the market for programming fonts vs. general desktop fonts. The market for a single font is likely a relatively small pool of designers / content creators who are spending their employers money, need it to complete a specific project, and who value achieving a unique look. The former is a larger market, who are spending their own money on a nice-to-have, and who don't particularly care about uniqueness.
The price point for fonts is set for people who intend to use the font to make money – like graphic designers. One could imagine a lower price point for private use, similar to media.
The font a programmer uses has absolutely no bearing on the products they produce or the money they make. Unlike graphic design, where a licensed font becomes a direct part of the sold product.