Well @budparr imagine you have 100k images in one Directory. Nothing is easy to find and reference. In the news business all is speed. Every once in a while you have to search an image for an article.
When the images are all together in one directory - it will drive you crazy.
Even when you use Subdirs under the static folder.
Every image can have a name with sense or just a combination of characters and numbers DCF37773_hhjd–goog.jpg for example.
Its really confusing.
And at the end, we have to realize backups of the whole system. And its best to have everything under content together.
With the new bundle feature it is possible to migrate from our custom WP and the db to hugo. And i am really happy about that.