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If I'm free to throw some ideas of what could have been done better  (for discussion and extension, maybe it would be a base for cleaned up requirements version in the wiki):
* not using Ruby on the backend ;-) * storage and duplicate files will be a thing; maybe S3 or Backblaze would be a good option, though I don't know what exactly current soup does.
* duplicate files detection, this happens on soup a lot. Not sure if we should MD5 uploaded content or maybe do some visual comparison magic (and pick the better quality on top of that?).
* GIFs should always be converted to videos. Save bandwidth, save quality, no scaling. Go gfycat-like! * webp whenever supported!
* Oh, speaking of which, not sure if the downscaling done by soup is needed, sometimes the files with _500 suffix are bigger (byte-wise) than the originals * when things fail, retry/remember. This is done currently for  unfinished posts, but not for reposts. * the way tumblr does reactions (as adding to the original post) sometimes seems appealing...

* an API for the mobile app. Oh yes, and a mobile app.
Reposted fromstate-of-the state-of-the

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