Django Pagedown Image Uploads
It only took 5 years. After years of dithering you can upload images with Django Pagedown.
Django Pagedown is a tiny library I created in 2012 to make it easy to add a Markdown editor to forms. It's crazy to me that it continues to get new stars on GitHub every week and is testament to Django's longevity that it's still popular.
One of the features that was request years ago (literally ... I think it was 2015) was to allow for image uploads. Initially I thought that this was something best handled as a add-on. Truth-be-told I wasn't using the library that much myself so I procrastinated on adding it.
Finally this year I was able to add it to version 2.1
meaning you can now easily upload images and have them automatically inserted in your content. It's definitely a good improvement and one I wish I implemented earlier.
Give it a go
If you have a Django project and don't like WYSIWYG editors, try Django Pagedown