Earlier quoted context omitted.
No, those things aren't comparable. Truffles have a functional role in a dish. A typeface does not have a meaningful functional role in a document, compared to the high-quality freely-available alternatives. This is like complaining about some kind of specially-carved or dyed truffle.
I respect you a ton (genuinely, I think you're the most interesting writer in the tech space), but you have a profound misunderstanding of the importance of typography if you think the only reason you'd need a paid typeface is the same reason you'd need a Hermes bag. I know you're a curious person, so hopefully you take this as an opportunity to open your horizons on the importance of it.
This to me is like the Menswear Guy on Twitter, who will explain in very great detail to you why the Hermès product is significantly better than the generic alternative. He's right, but he also understands that you buy the Hermès product to make a statement. Spend money on that statement if you want --- I do --- but don't try to pretend you have a right to it.
(i don't mean i own any hermes products; just stupidly expensive typefaces)