personality. i'm a extremely obsessed with klim foundry right now.
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klim has a great site to get you started. there's a lot of documentation that goes into each typeface he releases - and it's good insight into the thinking behind choices.
all the "why" of it. why this over that. why this typeface for this use, and this for that use. the feeling behind it and the techniques that evoke that feeling.
I feel like a lot can come down to cultural context. For instance historical influence and breaking from tradition.
Signifier by Klim comes to mind - klim.co.nz/blog/signifier…

Klim Type Foundry · Signifier design information
Signifier is a Brutalist response to 17th century typefaces. Acknowledging the processes and tools of digital form-making, Signifier’s digital immateriality draws on a deeply material past.
klim.co.nz
Thanks for linking. I’m basically a blank slate when it comes to type (all I know is you can’t get fired for using SF Rounded) … may dive in a bit this week!
It depends on what kind of typeface and purpose, but generally I’d say - craft.