We run events which have thousands of pictures every month. WordPress should have a way to be able to upload images associated to a post to a particular folder.
Lets say I have pictures of New York. Instead of uploading them to a monthly folder I should be able to tell wordpress to put them into /images/newyork and create that folder if it does not exist.
Honestly the images management is really sad for such a awesome product. Why are all images stuffed in giant monthly folders only is beyond comprehension. If it was only attachments I could understand but for galleries of images which are most of the time associated with a topic or subject I don t understand why the images should all be spread in hundreds of folders instead of neatly sorted by folders or categories.
I know there are a couple plugins that approximate this functionality but it become an issue to deal with upgrades and potential future code changes.
Please, please consider improving the gallery storage of images to allow an option to store images in individual folders as for webmasters during upgrades or moves to other platforms having to dig through hundreds of folders is a nightmare.
By having all images in individually names folders the media management becomes so much more efficient.