To be honest, I never found WordPress easy to use. It's all flowers and rainbows as long as I can find good themes and plugins. However, it starts going south as soon as I need to make a very small custom change.
I've always considered myself an above average web developer, my friends would always have Wordpress websites, and ask me if I can just tweak a few things.
Without hesitation, I'd proclaim I could easily make those changes!
Then I'd load their site, load their plugin/theme code and css files, struggle for hours to get the desired effect, and even if I got it to work, I would break every other part of their site.
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Denigrating anecdote aside, good job Matt, loved the story at the end.
I had the exact same thing happen years ago and I've never felt so helpless. Simple banner / color change. Ended up rebuilding the entire site from scratch it was easier.
Once you spend some time in the codebase and understand a bit of its legacy history it gets easier over time. A lot of plugins and solutions are aimed towards non-technical users and a lot of overlap. Where we might just write up some custom HTML others might install 3 plugins to make it work.
The overlap between plugins is crazy. It looks like every plugin comes with an entire SEO toolkit, a performance optimizer, a firewall and the kitchen sink. Unless you're very careful, you quickly end up with an unusable house with 5 kitchen sinks, no fridge, and 1 3/4 ovens that are perpetually trying to burn one another.
I think half the problem there is everyone offering half a house for free, but every company is offering a different half. No one wants to pay for the paid offerings that have all the features, they install one SEO plugin to get page metadata, another to get structured data / microdata, another to optimize keywords; when all they had to do was buy the premium version of Yoost, for example.
Thankfully there was a recent consolidation in a plugin called Admin & Site Enhancements (ASE). Probably got rid of 10 others with this thing. Includes duplicate post/page, admin menu cleanups & reorganization, hiding dashboard widgets, cleaning up the top bar, changing the login URL, an easy way to setup SMTP delivery, media replacement, hides the annoying admin notices, and a bunch more.
Initial setup of wordpress is super easy, but it gets very hard to maintain after a while. Updates require manual intervention, themes must be fixed, plugins deprecate. All of this adds a burden I am not willing to accept, which is why I moved all my sites to Hugo/Jekyll/Mkdocs (etc.) since about 2017.
How about PHP updates for major versions (e.g. 7 to 8), or how about maintainability for 10+ years? I was sick of all the work that emerged after a while for some simple sites. I have about 15 websites, all focus on a specific topic, with one or two updates per year. Wordpress is too much for this. Static sites can be moved around or hosted on the most basic nginx, whereas Wordpress requires a lot more.
I am not against wordpress in general, just that I found it not suited for my purposes.
I switched to ghost, at first it was a bit rough around the edges, but since they made the global cli. It has being quite nice. For blogs, would rather use that than WP. Of course I also prefer JS instead of PHP.