I struggled already 4 years ago:
I’m an experienced with CSS, HTML, JavaScript, C++, Java, shaders, OpenGL and many others. I’m used to learning new stuff. I really like how Hugo is extremely fast and capable. Thank you for creating such a powerful tool!
Unfortunately, every time I need to change something in my site, or create a new site a year after the last time I touched Hugo, I feel stupid and frustrated. I spend days trying things while looking at blank resulting pages with no errors or warnings. It could mean I’m a lousy programmer but I don’t have this issue with other environments. I know that if my job was full time hugo I would not have such issues, but at the moment I do struggle.
I take the time to write this because I care, I want to learn, and I want this great tool to be easier to learn by others 
Some thoughts and suggestions about the documentation:
- The documentation shows a grid of concepts with two columns. I find that confusing. I don’t know if I should read first the first column and then the second column, or should I read left right left right left right… Ideally I want to read linearly, starting from an overview and then looking at sections that build on top of previous sections. If you have many sections and they all refer to other sections I find it hard to disentangle.
- Same issue at Content management | Hugo There’s 21 “buttons” in that grid. Should I read everything before I start? I miss order. The first article of all is about GPDR (About Hugo > Overview). Is that the first thing I should learn about it?
- Lookup order. See Template lookup order | Hugo. That page includes massive lists of lookup locations. What should I do with that information? Memorize it? Or if there’s 20 locations a file could be placed at, how do I choose one of them? What’s the purpose of those lists? Also notice how line breaks make the list unreadable:
- Themes: many example get you started by choosing a theme. But what if I don’t want a theme? I think a theme makes sense if you are into designing sites for other people, or if you want to reuse your design in many sites. But that’s not the case on any of my sites. I just need a one-off website. So going to the topic of this post: a tutorial would be super useful in this sense. How do I go from nothing to a web site, and the journey from one to the other, which is often not a straight line, but you try things out and make changes along the way, you add features, change, and remove them.
- How to work around the fact that many of you are very experienced, which may make it difficult to see things with the eyes of a beginner? Maybe watch someone learn without giving any hints? And this is not necessarily about being a beginner with building websites, css, html or js, but with all the terminology introduced by hugo or other static sites generators (kind, type, archetype, section, format, layout, theme, template, block, list, taxonomy, partial, shortcode, front matter, etc).
- Sometimes new features have been introduced that enables a new way of doing things. It would be great that such a feature comes with a tutorial of how to go from the old-way to the new-way, and not only a page in the documentation that describes the new-way. For example I just went from having media inside static into having it inside per-post folders, and it was not straightforward to figure out.
I think the documentation contains all the needed bits and pieces, but is missing a guide about how to learn, the big picture, the process, why to do things in one way or another, suggested approaches, pitfalls… I’m definitely going to check some of those videos mentioned above to see if that fills the blanks.