Does anyone know a good resource to learn about fonts and how to pick and match them? I'd like to know if there is more to choosing a font than just scrolling through all of them and stopping when it looks okay.
As usual, learning to see good fonts is a matter of recognizing bad ones first. You'd want to look at reviews of bad fonts, more-or-less detailed.
Then there's also the matter of the font style: a decorative font may easily have an untasteful twang to it (e.g. “playful” ad fonts), or be overly pretentious for the task. This is also a matter of looking at a lot of examples and thinking of what they make you feel.
These are just the basics, and designers sometimes diss fonts that look fine to me. But these help. Also, IMO learning to see and apply the proximity principle covers a lot of design, including typography (e.g. line spacing and paragraph positioning).
I haven't read the latest version which says it's updated for the web, but even the copy I have is amazing.