Why does it look like there has never been a backup of my old watch? If it is stored in the iPhone backup, why doesn’t it say that?
The backup of the old watch was running a version of iOS that greater than the version of the new watch.
The back up from my old Apple Watch was running a developer beta which is presently WatchOS 7.2.
The brand new watch, being unprovisioned, could only run up to WatchOS 7.1, the current newest public release.
After all of this repairing and unpairing is there still no backup of my lid Watch?
The backup was visible when restoring the old watch. Because it was a version of WatchOS it knew about.
If Apple knows I have one watch and I order a new one, and am setting it up, why doesn’t apple ask if I’m just upgrading and handle the whole process for me?
I think this is because Apple does not have enough customers who are in upgrade situations like this. It definitely could telegraph the situation to the user. My recommendation to Apple would be:
Show all backups of a WatchOS, including those that can not be use. Show it with the version number but disabled. Offer an ( i ) icon next to the backup it you can tap that explains that the watch you're restoring to can not run this backup.
It should explain that the new watch must be updated to at least the version shown on that backup in order to use it as a restore.
I forgot that I had provisioned this watch to run the newest WatchOS. I re-paired the new watch, provisioned it for the beta, unpaired it again, and then was able to restore the backup from the old watch.
Wasted a lot of time trouble shooting this, so I hope if finds someone in the future or Apple adds this workflow.