I am not sure that anyone is trying to discourage people from entering the field of type and design. A child's handwriting (or indeed mine, which is very child-like) can be read but that does not mean that it is readable. In order for the consumption of type to be a pleasurable experience, its design must be considered. Design involves the consideration of the space between foreground elements, the contrast of foreground and background elements, the grouping of foreground elements into familial sets (e.g. beginning, middle and end) etc. People have been concerned with this subject for millennia...
Western fonts derive from Roman lettering which were carved in stone. The dedication inscription at the bottom of Trajan's Column is arguably the most sophisticated example of this. The text at the top of the inscription is larger than that at the bottom so as to appear perceptually uniform from the point of view of the viewer (who is located significantly below the inscription).
Letter forms are weighted towards the bottom. The designers of Bauhaus (who were very reductive in their thinking) tried to do away with this and produced super-regular typefaces based on squares and circles. They quickly realized that this produced a result that humans find unappealing and unreadable.
The digital age saw the adoption of characters that were dimensionally uniform (i.e. monospaced fonts), such as employed in the comment widget of HN. Of course such fonts are easy to digitally express, but as I am sure you will agree for a printed document the effect is clunky and lacks flow.
It is this ongoing dedication to form, structure and readability that is at the heart of effective typography.
I am not a typographer, but have worked with many in my job. I often mock-up page layouts and show it to my designer for their approval. Of course, I think I have done a marvelous job, but their response is always the same: 'yeh, really nice. However, maybe you change this space, this color, this font etc etc'. The result is always 100 times better.