3 notable reasons why a lot of people struggle with htaccess are a lack of a need to use htaccess often, regex(regular expressions) and debugging.
When most webmasters use htaccess, they search for the code they need via stackoverflow or whatever else comes up in the search engine they use. They copy and paste the code in their htaccess file and as long as it works the way they want it to, they're done with htaccess possibly for a very long time if not forever. Most webmasters don't fully understand the htaccess code they are copying and pasting. If they do end up having to use htaccess again to do something that can be potentially complex, they struggle due to the lack of experience studying it and using it. The lack of a need or incentive to use htaccess often is one of the main reasons for that lack of experience. One thing people can do to overcome this challenge is to study the htaccess tutorial that apache provides on their official website.
Lack of knowledge and experience in using regex can be a big factor in why a lot of people struggle with htaccess because regular expressions are used a lot especially when using the mod rewrite aspect of htaccess to manipulate URL's. There is a lot of depth behind regular expressions. Regex is a complex concept and can take a lot of time, study and practice in order to become good at using it. Even for programmers, regex can be challenging because programming books and/or tutorials can only teach about regex so much before moving on to another programming topic/concept. A lot of programmers don't need to use regex a lot or enough to have an incentive to become good at using it. It's situational. Regex by itself is complex enough to be worthy of a book or tutorial dedicated to it alone separate from the programming books/tutorials that briefly teach about it so it's important for the programmer to put extra effort into learning regular expressions outside of the programming books or tutorials they may have read if they want to be good at using it and understanding it.
Debugging htaccess can also be problematic. Even though it's possible to see logging information for htaccess, some people tend to struggle with setting up a debugging environment for themselves since it's not intuitive. Trying to use htaccess without debugging can be like shooting in the dark and just hoping things work the way you want them to. It is very different from debugging a programming language with an IDE that comes with a built in debugger or a server side web programming language like php that will show you if your php file has an error, exactly where the error is in your file(the line number) and the description of the error. Knowing the problem/error information makes coming up with a solution a lot easier. The htaccess tester is a web tool that can somewhat work for debugging htaccess especially the mod rewrite aspect of htaccess.