I think you are missing the point. The font curves/shapes/beziers are not copyrightable. But the source code and resulting font file is (everywhere). Fonts are licensed just like software (or more like software plugins).
So you can take any typeface and trace/redraw it just fine. But you can't use the original font files unless you have proper license.
Fonts might seem trivial but actually there is a lot of engineering going on underneath. There is whole programming language underneath that allows fonts to do what they do, spacing between characters, how they should be rasterized on screens and also making them widely compatible.
So in same way as one would expect “its just a CRUD app” it should be trivial computing task to make a “different” copy. No unless you do some decompilation of the font which is breaking the license.
About why people bother… maybe the biggest issue typography (and lot of design in general) have is that if done right it's mostly invisible or natural. You notice typography only when it's done badly - it's very subconscious. That doesn't mean it's not ongoing topic with experts dedicating their lives to it. And for them even differences between variations of Helvetica matter. If you look around yourself you will have typography absolutely everywhere - you have probably 1000s of different fonts just in your home. You probably don't notice them but you would if our society standards were lower.
That's exactly what I was wondering, since I vaguely remember that all this "copyrighted fonts" silly business boils down to the exact source code, and the same shape can be represented a hundred ways. So, what's the big deal, anyway? I never tried to do it, but I'd assume that to make a "different" copy of a font with minimal human intervention must be a trivial computing task by now. Sure, in theory there are subtleties like many possible ligatures and kerning, but I doubt it's really that critical. And it only matters if you only have a picture with so many latter combinations. If you have the actual font file, you have full information anyway.
And if so, why people still even bother with all that "font licenses" stuff and such? I'd think the only reason to buy a font by now must be when design studio actually does custom work for you. And the emphasis is on "custom", because it isn't truly "for you": anyone will be effectively free to use it after you use it once anywhere.