I recently started using it and find that after reorganising the confuddle left by the core system (and a few forays into media plugins which turned out to be less helpful than they promised) I have been able to organise the layout to a more logical structure.
uploads
— ads (media used in the few ads onsmy site)
— embellishment (mainly logos, badges and decoration)
— events (contains images only used in events)
——- 2018
———– 01
———– 02
———– …
— magazine (archived pdfs of my magazine’s print edition)
——- 2018
———– 01
———– 02
———– …
— news (news items)
— pages (images used in static pages)
——- 2018
———– 01
———– 02
———– …
— places (images of venues used throughout the site)
——- BlandfordForum
——- FontmellMagna
——- SturminsterNewton
The biggest, busiest part of my site is a calendar which aggragates events for my part of the world so it gets very cluttered with ephemeric media. It also has a news section and local archive so also has a requirement for a growing collection of static media.
I give each media item a human friendly name and upload it to where I think its logical home should be. When I add it to a post/page/event I can search for it using the name I’ve given it, and check the URL in the media selector to confirm that I’m using the one from the right folder.
I tend to clear down the events calendar to get rid of past events. So – as it’s now well into 2018/02 I know I can delete all media for 2018/01 events without accidentally deleting places images which will be needed again (if not already in use), media used on static pages, media used in the news section etc.
I don’t use the premium version of the plugin. The free version is working well enough for me at present – but it is early days yet.
Hope this helps.