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The issue with any dynamic site is security. You can't set up Wordpress and forget about it. There has to be some mechanism for updating to the latest version for security (which may break any plugins/themes).

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WordPress has had one-click updates for years and makes it easier than any other CMS I've seen. It's been doing a fine job and powering 25% of all pages on the net and growing.

The problem is that updating plugins very often breaks stuff.

I've been running a heavily customized WordPress with literally dozens of plugins since 2005 and that has most definitely not been my experience.

One I can remember is that Facebook's official plugin stopped working and we had to switch to some other social integration plugin.

Another one was the embeded media player which just disappeared. That was somehow related to shortcodes.

I've only had that happen twice in a dozen years.

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