Dynamic content in a widget

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I have a little to none experience in developing a plugin or widgets, but I believe this is certainly doable in a custom WordPress theme.

  1. Output an ajax multiple file upload form in the sidebar. Link
  2. Handle the file uploads and save them as attachment. Link
  3. After you get the attachment(s) ID, save them as an array in the user’s meta e.g ‘sidebar_image’. Codex
  4. Back to the sidebar, check if current user already have the ‘sidebar_image’ meta.
  5. If she does have a value, then just create a attachment query, according to the meta value. Codex

If you want this method as a widget. The function on step 2 and 3 will be the same if you use a proper ajax method.

Hope this help.