This is a broad over-view of the feature work of the Multimedia team; it does not cover bugs, but instead the broad-brush of items to be worked on in the next few years:
Flickr uploads for all: Users can cross-Web upload files from Flickr without being a sysop β task T90004
VisualEditor graph editing: Users can create and edit automatically-generated graphs within VisualEditor β task T89287
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Next up
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Better video playback: Users receive a more modern and higher-performance video playback system β task T93544
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Design/product work needed before it can be worked on
Third-party uploads: Users can configure third party services to allow cross-Web uploads (like with Flickr) on-wiki β task TBC
VisualEditor sheet music editing: users can create and edit sheet music within VisualEditor β task T49528
Structured data: Users can store meta-data about files in a structured way β task T68108
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Re-use notification: Users receive an automatic notification when a file they have uploaded is used on a Wikimedia article β task T77154
Blocked items
NΒ Blocked on security vetting needs: Users can upload and view 3D files β task T3790
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Lower-priority backlog
Drag-and-drop VisualEditor uploads: Users can drag-and-drop files onto VisualEditor to trigger a media upload β task T40031
Copy-and-paste VisualEditor uploads: Users can copy-and-paste files into VisualEditor to trigger a media upload β task T39932
Drag-and-drop WikiEditor uploads: Users can drag-and-drop files onto the wikitext editor to trigger a media upload β task TBC
Copy-and-paste WikiEditor uploads: Users can copy-and-paste files into the wikitext editor to trigger a media upload β task T23557
Mobile uploads: Users on mobile devices can upload media β task T97169
Edit-as-you-use: Users can modify media files (e.g. cropping, skewing, rotating, re-colouring, etc.) through the editor rather than re-downloading and modifying β task T9757
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βNote that "Uploading", though it sounds simple, requires extensive security validation and verification, which is frequently exceptionally hard and is normally the stumbling block. It also generally implicitly requires the work for these files to be viewed by readers.
βThis covers modifying on-wiki files that are uploaded, as well as creation and modification of non-file media types (like timelines, charts, etc.).