Yeah, you're using the Internet as Team A in the author's example. You're looking for images of fonts. The people that made those images bought a license to use the font to make images, so it's fine if they share them with you.
None of that guarantees you'll be free from legal concerns, of course. Maybe the original image author didn't have a license. Maybe the licensor thinks they can change the terms of the contract at will. You'll probably be caught in the middle of all of this.
My take is that the biggest problem you'll find is naming your free fonts. Someone probably owns the word "Helvetica", so you'll have to call it something else. Someone looking for a font will then not find yours, and will buy a Helvetica license.
Back in the day (Windows 3.x era) I used to use cheap lookalike fonts from shareware compilation disks/CDs. So there was like a Palatino clone called "Palamino", a Cooper Black clone called "Cookie", an Optima clone called "Proxima", etc.
You can still find fonts like this on font sites all over the web.
The Atari ST used to come with a font named "Swiss". It was basically Helvetica and was named that because "Helvetica" is Latin for "Swiss" (as in "Confoederatio helvetica").
None of that guarantees you'll be free from legal concerns, of course. Maybe the original image author didn't have a license. Maybe the licensor thinks they can change the terms of the contract at will. You'll probably be caught in the middle of all of this.
My take is that the biggest problem you'll find is naming your free fonts. Someone probably owns the word "Helvetica", so you'll have to call it something else. Someone looking for a font will then not find yours, and will buy a Helvetica license.