There are a few pretty impressive font apps out there. My favourite is Font your Face (http://drupal.org/project/fontyourface). Only problem is it only allows for you to use existing sources. i.e.
Is there any way to add a "source" that is effectively grabbing files off the server? I want to be able to upload my own fonts.
The @font-your-face module now includes a local fonts module that does exactly what you've described here.