One thing is that traditionally users don't buy fonts. In the past, the only people you expected to get any money from were people who got paid to set the type. You might spend months to years working on a single typeface and in that time a considerable amount of work had to be done to market it (done usually by the foundry you were working with), because after that much time a real flop might mean the end. Over the last few decades the barriers for creating and distributing type have definitely shrunk significantly, but there's still an issue over how type should be licensed and exactly what it needs to compensate for. Many typefaces are created by people who are otherwise employed as graphic designers or illustrators, while the individuals who are solely type designers have to contend for their living with type only in what is now a sea of free or corporate subsidized fonts (i.e. what came on your system).

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If what I just typed makes no sense at all, I blame either my insomnia or the ambien which I refuse to take for it.