Pre-define bulk upload settings or prompt the user to choose their settings each time they upload

The scenario is a user has organised a bunch of folders and files which will be stitched together to form a book online. The idea is users will be able to drag & drop / click to upload all of these files and folders at once, rather than doing them individually.

Added complexity: users structure their files and folders differently which often calls for custom import settings. There's 3 key settings that vary depending on the user and the book they're creating.

  1. Create a chapter per file (very common setting turned on)
  2. Number chapters (useful for majority of users)
  3. Remove leading numbers (users will add numbers to their folders / files to create a custom order, for example "01__My First Chapter" will be ordered before "02__Bees can fly".

When a users first creates a book, it's significantly likely they'll stick to the upload settings they've defined as that's how they're structuring the book in their file management system.

I have two workflows I'm having difficulty deciding between. One pretty seamless, the other adds a layer of security / validation of how things are being imported later down the track.

  1. Let the user pre-define their bulk import settings, and from that point on any files that are uploaded will inherit those properties. This can be changed manually in a separate options menu, but when the user uploads their files, they upload and are modified instantly to match your import settings. To me this would be a seamless approach so the user can add any additional files in the future and they'll be presented as they've defined. However some situations might call for NOT creating a chapter per file as they're being uploaded and would mean the user would have to update their settings beforehand in order to ensure they're uploaded how the user expects. Or upload files individually and just re-order / change them if necessary.

  2. We could still do some pre-defined settings when a book is initially created and empty, however in the future if the user wants to upload multiple files, we provide the user the ability to configure their import settings before starting the upload. What I don't like is that this introduces an additional step when uploading files in bulk instead of a seamless interaction like google drive.

Would be keen to hear your thoughts. Originally I wanted to have it so you could seamless upload whatever content you wanted, and could configure the presentation easily later on if needed — however due to the dev infrastructure it would be a significant effort to do this.

I've found it difficult to find examples of bulk import settings / configuration as you're uploading — usually it just starts and that's how it is so this is a kind of unique workflow.

Cheers.