Thank you for looking into this, Quinn.
(The VM I had used had no snapshot (stupid of me), so when I borked it, I had to ditch it and start over, installing a new system from scratch, and then installing Xcode and all the other tools again, which took me quite a while that I would have liked to avoid. Also, I'm glad to be using VMware on a Intel so that I can make snapshots, as the support on Silicon is still a bit ... lacking in this regard :)
Ah, creating a new user - of course! I should have known that.
Also, there's another related issue:
In my testing with a fresh VM I noticed that when I download two versions of my app (release and beta, both signed with my dev ID and notarized, and then both downloaded from same server and thus quarantined), I found that macOS prompted me twice for the "Local Network" permission, i.e. one for each app version I launched. That's different from TCC permissions, where a single permission was always applicable to ALL versions of an app with the same signing ID. And even worse: Even though the System Settings then list the app twice, both use the same name even though I had named them differently, and right-click - Show in Finder shows the SAME app instead of the two separate apps that required to be acknowledge when they accessed the network. So, that appears to be another (minor) bug, though I don't know which would be the proper behavior: Require the permission only once for all apps with the same signing ID, or require them for each version but then list them also properly as individual instances with their own names and file system paths.
Can you confirm this misbehavior?