Plex Cloud Sync Status Forever "Waiting to be uploaded"

I know there’s plenty of issues relating to features that once worked, but here’s one for a new (new-to-me) and recently discovered issue of Cloud Sync not syncing.

Syncing to iOS works fine but Cloud Sync items are stalled. I reauthorized Google Drive and Dropbox without success.

Logs attached.

Let me provide a quick rant:
This new issue with PMS was disappointing and makes me doubt Plex’s commitment to paying customers. I work in IT and know coding can take time, effort and headaches. But if you break a working feature, you should be agile enough to roll back bad changes. (Out of curiosity, what does Plex use to manage your code? SVN? Git?) With months of DVR recording errors in the forums and also experienced by myself, I can only imagine the technical debt accrued to fix these issues. But, please make some effort to show the paying customers that change is coming.

If you were to ask me, the first thing to do would to stop adding new features! (VR?!) Rather, fix what is wrong! Make a commitment to us your customers that the month of February will have all devs (or a focused team) only work on the “100% complete” recording bug. Make DVR Great Again! Then March will focus on the next feature that has been broken. The next broken feature is the next month’s focused feature fix. etc. Lather. Rinse. Repeat. Do this until all the broken features are fixed. Then, roll out new features.

These FFF (Focused Feature Fixes) may have to have Plex get out of their comfort zone. Namely, rather than only forum posts providing logs and delays between answers, you may have to schedule phone calls to contact customers and work closely with them to collect logs. Remote desktop access. Something to get results.

End rant.