Designer Frank Chimero is redesigning his personal website and is posting about the process, with a few sections dedicated to type:https://frankchimero.com/blog/2019/redesign/
I find a behind-the-scenes look into the decisions being made, comparisons, and how someone articulates all that to be interesting.
I do agree with his point. I never understood why webfonts had such a different value from print or even any other kind of usage. With typekit and so on, for you to pay a monthly makes sense, you're diluting the value with the time you use it, makes sense but paying extra just because you're using it on the web? Seems a bit a rip off. If you pay the full price for the font you should be able to use it everywhere. The argue could be that font designers are diluting aswell the value per usage but you as a font designer had exactly the same work so why dilute that way? Makes it harder for "clients" to buy fonts all this extra hassle they will have to be able to use something.