It’s a task that can be easily tackled using wp_handle_upload and wp_handle_upload_prefilter (e.g.: Give users a maximum upload capacity; limit the number of files a user can upload OR limit the number of files per upload).
Luckily someone already did this, as a plugin: Upload Quota per User. It’s pretty old and seems unmaintained but tested on WP 4.9.9 it works.
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