People are often clueless about the technical and legal difficulties of proprietary fonts on the web.A cynic might suggest that this is because of greedy foundries insisting on a rental model for web fonts, sometimes one so complicated that you need lawyers to figure out what you're actually paying for if you sign up. If they'd tried that with print fonts, most of those foundries would never have made it this far.
What really surprises me is how readily the web design industry caved and paid up, particularly given the relatively poor quality of most early web fonts even from the commercial services, and how many of them remain poor even today.
I'm hoping that sooner rather than later, the prevalence of good quality and fully specified free-to-use font families will force a change in the industry. Personally, I'd be happy to pay a reasonable amount for some good professional fonts. In fact, I have, from my own pocket and not any business's, on several occasions. However, I have no interest in locking myself, my businesses or my clients into ongoing payments for fonts when essentially no other stock resources work that way, and even less interest in hiring a lawyer to figure out whether someone's web font licence covers a particular not-entirely-standard use case.