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Also worth noting that entering <p>text</p> or </br> tags does not work.

Link to site?

https://obfessed.com

[Moderator Note: Please ensure that you are embedding links correctly in your posts.]

Here is a specific post showing the problem:

https://obfessed.com/festival/lollapalooza/

Long shot: Any chance you have used code in your functions.php such as:

//Remove <p> <br> tags
remove_filter( 'the_content', 'wpautop' );
remove_filter( 'the_excerpt', 'wpautop' );

which suppresses <p><br> tags?

I suspect a plugin. Standard advice:
– Deactivate all plugins
– If the problem disappears, reactivate them one by one to find the culprit.