– Goal ? Legibility | Readibility.
– Appropriateness ? Design Intent | Aesthetics | Mood | Personal choice | A few technical considerations.
– Tips ? Plan your hierarchy | Consider what others have done already | Experiment the easy way | Avoid anachronisms | Avoid trite correlations | Consider an extended type family | Stick with the classic combinations | Use a limited palette …then, Break the rules.
The non-typographer’s guide to practical typeface selection by Cameron Moll
On Choosing Type: First Principles by John Boardley / I Love Typography
Choosing & Using Type by Daniel Will-Harris (old but excellent article).
Technical Web Typography: Guidelines and Techniques by Harry Roberts
“What Font Should I Use?”: Five Principles for Choosing and Using Typefaces by Dan Mayer
Best Practices of Combining Typefaces by Douglas Bonneville