Hello WP, I have recently stumbled across a new service called Typekit which I tried on my personal WP blog (not the one here at WP.com) and thought it might be a cool revenue opportunity for you guys. Typekit has free and paid options to embed fonts on any domain using CSS font-embed and other tricks.
There are other up-and-coming font embedding services that can best be described as "iTunes for web fonts" besides Typekit, so even if it's not them, it may be worth partnering with one or more font foundries to split some of that yearly subscription revenue. Once people start seeing cool fonts on other sites they will demand them too. This would also open up a huge range of new options for theme designers.
If you want to roll your own and avoid partnering, you can also go the Cufon/sIFR route for headings and charge a small upgrade fee too...
The blog I need help with is bkendall.biz.