I think modern fonts include hinting software and stuff like that.

If you produced a bunch of screenshots of the output at various sizes, and then asked an LLM to convert to ttf or whatever, I’m guessing that’d be OK. I’m not an expert in this stuff though.

Brand fonts are typically a specific license by the original creator of the font, often together with some adjustments (e.g. big companies often need additions for global markets that were not in the smaller original font)