I recently had a problem when trying to create an image gallery with Toolset in that uploading many images or files into one Types repeating field can be a major hassle. There were many other topics on the forums here with similar issues and no good solutions.
I searched online for snippets and various answers and ended up making a plugin that outputs and processes a form on the frontend to create a new "Gallery" post, which includes a multiple image uploader for my custom field, "gallery-image". I'm sharing it with the Toolset community in the hopes that it can be helpful to others trying to upload many files into a repeating field at once.
Here's the Github: hidden link
*Note, I am not a coder, so this is a really basic plugin with little security. Please limit the form's display with Access or some other kind of plugin so that only Editors / Admins can use it.
Thanks all! Hopefully one day the CRED development team can create a more native solution.