Currently, there is a flat 100MB cap on video sizes.
This is rather restrictive. There's a rather large amount of videos that have had to be compressed to fit here and have significantly better off-site versions.
This limit exists partially to prevent upload of videos that are absurdly large for what they contain. For instance, a lossless conversion from MP4 to WEBM will be absolutely huge for the content. However, it does not do this well - short but extremely badly compressed videos slip through, while preventing proper archival of longer or higher resolution videos.
This proposal is to instead limit WEBM file size by contents, in particular the number of frames and the resolution. This would allow for preventing uploading video far too large for what it is, while allowing uploading high-quality videos that otherwise could not be archived without destroying the quality.
This is doable - the site already gets upload statistics to determine duration and resolution, which could be reused for such a system.
There would still have to be an upper limit of course, and the actual details would be up for discussion. My first thought is simply a linear relation between the total number of displayed pixels and allowed file size, along with lower and upper bounds.