I don't think that the learning curve could really be said to be the problem when you're talking about a word processor that deliberately deletes three days worth of saves when it crashes.
That's not even the argument I'm trying to make. The crashing issue is just bad software. There's no argument against that. It's implicit in the points that I make that I'm referring to his frustration with bloat and his perception that some rather advanced features should be "easy" (chapter markers, for example). In order for a machine to parse text, it must be given some specific information. It cannot read the language and understand where a chapter begins or ends based on some arbitrary value that we have in our minds. We must use the machine's language, because the machines are not able to understand what we mean. Hell, many humans frequently fail at understanding what is being communicated to them.