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I didn’t set it up this way, but having so many images in the main uploads folder with no dated sub folders makes it very slow to access that uploads folder through cpanel, ftp, and is more difficult to work with when backing up.
So, I just want all uploads to be put into dated sub folders from this point on so that one folder doesn’t become impossible to work with once there are 100,000 or more images in there.
Are there any unpleasant surprises that can happen if I put WordPress settings back to default and tick this box? : https://i0.wp.com/answeryourtech.com/wp-content/uploads/2019/03/how-change-folder-upload-setting-wordpress-2.jpg
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No
Short answer: no.
Long answer: Aside from probably needing to cull your uploads folder, changing the file structure doesn’t actually have much in the way of benefits. Dated sub folders are a pain in the a as a dev. Particularly when rebuilding etc. personal and company policy is all builds upload directly to the uploads no dated folders. Given that is how it is done at scale across thousands of sites I’m not likely to be ever convinced dated sub folders are better. But you do you.