In that case, they should have "blog only" licenses, or "small-website only", or "small business documents only".
People buy lots of stupid stuff. If they buy hats that their characters can wear in a computer game, they will probably buy fonts, too.
Sure, but you're going to have to give them some time, because they're only just now figuring out how to license web fonts in such a way that they're tied to sites or pageviews instead of granting blanket permission to use the fonts for websites, magazines, and investor reports.
In the meantime, you're not where their bread is buttered yet, so the urgency isn't there.
Obviously, the other issue is that a publication will pay a gigantic amount of money for a typeface, but HN readers will only reluctantly spend $21. Rather than trying to bridge the gap, it makes sense to sell to the party that values your work the most. Again, this is a very common and sensible pricing dynamic.
Operators of $5/yr SAAS services take heed!