Image uploads are now turned on. I’ve added a few file extensions (psd ai eps tiff tif) to those that are standard on multisite (jpg jpeg png gif pdf).
We’re moving dotorg onto new hardware soon, but currently, uploads are limited to 1MB for now, with an additional cap placed on the site as a whole. Test away, and let us know if there are any issues.
You do need author permissions to upload images in WordPress, so John now has the ability to promote users.