After the advice I found on this sub, I switched from DEPNotify to swiftDialog (thank you all for that). However, I am having the same problem that I had with DEPNotify:
Most of the policies in the array run without any issues - these are application install policies. They complete consistently without any problems.
The policies that do not run correctly are the ones that set the Dock, rename the computer, apply the wallpaper, and (most annoyingly) Log Out the user via swiftDialog. It seems like they are the ones that rely on SystemEvents or osascript, etc... When I check in the Jamf Pro Policy logs, they are not even showing as being triggered so I can't get the cause for failure.
Once the user logs out, enables FileVault, and logs back in, the policies run correctly (except for the fact that I need to give PPPC policies to Finder, which I don't seem to need on first login).
Is there something that is either running or supposed to be running within macOS on first login that is causing these things to not even trigger or run correctly?