I suck at picking fonts. I wish there was a site which could recommend fonts based upon some input. I don’t mean the usual serif/sans/slab type choices, more like:

headline, straight serifs, thin, classy, professional, timeless

and it would spit out the perfect headline font which matches all my requirements, as well as recommending complimentary fonts for other common text (body copy, block-quotes, secondary headlines, etc). Ideally it would create your complete CSS stack with sane substitutes for non-websafe fonts and integrate with Typekit or similar.

At present I am having to make do with:

• Awesome fontstacks
• Typekit love
• and browsing Typekit by Tag