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Are there any fonts that have random variations for every letter (is it something possible to do with curent font systems?)

That would be nice to create fonts that look more like real handwriting.

Contextual alternates and ligatures are on my todo list! :) https://ctan.org/tex-archive/fonts/punknova?lang=en is an interesting model.

It is possible, and frequently done in higher quality handwriting style typefaces.