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I’m curious what roadblocks users are facing or maybe some experiences you wish were improved or easier to use.
Could be pluggins, hosting, user experience, mobile usability, where do you experience the most hassle?

The JavaScript APIs are not (fully) documented e.g., `wp.media`
The usermeta table is a terrible structure that requires SQL Queries to be more complicated than you would otherwise need. I usually create custom tables to get the functions I need.
Gutenberg + widgets redesign are a dupster fire and I wish I didn’t need to install that many plugins to have basic functionalities like duplicate posts and classic editors.
The database structure is piss poor and WooCommerce shoehorning most of its data into wp_posts is an abomination.