Is there a website/app/service that will ask you what features you want of a font and it will show you recommendations?
What's the emotion to be conveyed? Where's it used? (Heading, wherever)
Then, display the top font, and a visual list of choices. I suppose that one could also link to free OSS fonts as well, but that would likely have to be second-tier compared to using what's on the computer already.
"So You Need a Typeface": http://julianhansen.com/index.php?/alternative-type-finder/
The path to Comic Sans is appropriately humorous.
something like that?