As a designer, I run into issues with font licensing all the time. Over the past year, there has been a large push on the internet to use and integrate native fonts into standard web design, by distributing a copy along with a web page using the @font-face CSS3 tag. This of course presents a massive legal and creative wall. Any designer worth their salt has access to a range of high quality professional fonts created by respected font foundries, none of which can be used legally in a native font format. This leaves designers with a broken selection of matched fonts that have a tendency of kerning and spacing issues.
Even as support for @font-face is still in its infancy, there are free resources available to help developers.
The first place I go when looking for higher quality fonts with open licensing is FontSquirrel. Not only is the collection huge, the site has a wide range of built in tools to make implementing @font-face even easier with pre-packaged @font-face kits, and an @font-face generator.
[ FontSquirrel ] [ @font-face Kit Generator ]