Using async chunked uploading may be a possible workaround for T128358: Uploading 1.2GB ogv results in 503, but Site.upload does not yet support so.
MwJSBot.js (used by bigChunkedUpload.js) has an implementation of this and is known to succeed on larger files than pywikibot can achieve (T128591#2085330 succeeded on 1.7GB file).