I stumbled onto a little trick. It's not a multi-file upload, but it's much faster than the "add new...file" route.

Edit any object that exposes the html editor for manipulating the body text.
Click on insert image tool
On the "Internal" tab, navigate to the folder that you want to upload to

Click "Upload" just right of the Search box (browse dialog will open on right)
Select file to upload and optionally add a title and description
Click blue the "Update" button
Repeat above three steps for each file.

When done, click cancel to discard the changes that you made to the edited object.

Note, you can upload any kind of file, but only image files will appear in the navigation window on the left. Rest assured, though, the files do get uploaded. If you back out and go to contents view, they will be present.

We need this too. Would save many, many hours. Doesn't need to be fancy--just use the filename populate the container fields. Quite happy to add better title and description after the upload is complete.

This would be very useful for us, since we'd like to have our Naturalist website as a photo repository.

This may come with Plone 5 but we don't know when that is.