A List Apart just published an excellent article looking at the state of fonts on the web. It covers all the reasons to be optimistic as well as a few things to be concerned about. The article links to a funny-because-its-true open letter to commercial font vendors that highlights the backward state of most font foundries by stating quite simply:
I want to see a browser-friendly and well-categorized selection of fonts. I want prices that make sense within the overall cost structure of the sites that I make. And I want licensing terms that give me the flexibility to do what I need to do. I don’t design signs, or magazines, or advertisements. Those folks have their needs, and I have mine. I make web pages.
I have absolute faith that the services which offer web fonts like TypeKit are going to proliferate, so these matters will feel like distant memories in short order. Just take pity on the poor sods who, in the meantime, have to buy prohibitively expense licenses because they selected a great looking typeface for a print piece and then found themselves needing to deploy it dynamically in a Flash site.