I feel for font foundries, it's hard work to make great fonts. People want great fonts. Actually paying for them is kind of an afterthought. It sort of seems like some of the big ones should put together an MPEG like group, get all the major foundaries to join and then have a couple licensing options. Some annual fee based upon your use and application and you get to use all the fonts. If it was like $120 or less for personal use, I think I'd buy the license for the family. I suspect they'll want 10x what I think is reasonable.
They're a bizarre economic phenomenon. They basically sell casino chips (stocks) and use bureaucracy (friction and complexity), PR (lies), and intimidation to goose their value.
I think this strategy only works if you have enough marketshare and vendor lock-in that customers can't easily leave and you have enough money that you can get new customers by acquiring other companies.