I've been working on a GridField component that allows to create records that contain images in bulk. Basically uploading a bunch of images and editing some of the DataObject's fields on the fly. (This makes uses of UploadField and how it is used in asset admin)
I've got the code here: https://github.com/colymba/GridFieldBulkImageUpload
and it seems to work OK apart from a few bugs and some improvements needed.
One thing I have a hard time understanding is why the "Drag & Drop" area doesn't always show up in Chrome? If anyone has time to test and/or comment I would appreciate it.