You could easily set up a system where media is embedded in the chat feed, but is stored externally. This is already possible. If I upload externally and then paste a link, but if you use the Google Drive API you could set it up to allow me to use a specific Google Drive folder to store any file in excess of what Discord supports.
Really, this suggestion just removes a few steps, but has some added benefits. For example, the server owner could have to option to allow all files uploaded in excess of what Discord otherwise supports to go to their own Google drive folder unless the user overrides that with a request to use their own. If subfolders use the username of the uploader, then it would be a simple matter for that user to later change their mind and automatically have their files moved to their own Google Drive without disrupting it's appearance on any logs.
The end result would be the ability to upload files of any size without Discord having to deal with the required storage space.
If you feel that this would prevent people from paying for your Nitro and/or boosts, then make this a level 1 perk or something. You'd get money out of someone else hosting data, and I'd be able to seamlessly use Discord without limits.
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