Jason Parker wrote:
I was maintaining yesterday those permissions were “fixed” and on restart… poof. There went my ability to use my laptop. No idea really.
Can you provide more details about what this "maintaining" was that you were doing?
There are multiple things going on here.
1) As others have said, Apple changed the format of it file system a long time ago. It is just crazy complicated. To try to simplify it somewhat, just think in terms of the system and data volume.
You have no control over the system volume. Apple owns that. Your data resides on the data volume where you can make changes.
2) Did I mention that it was complicated? Sorry, I didn't fully explain. It's more complicated than that. Apple then magically "fuses" the system and data volumes back together into a fake volume. You have virtually no control over the root directory of this fake volume. (See "synthetic links" for the one exception.) And there are a few additional layers of complexity that I won't even bother mentioning here because they aren't relevant.
3) I can't speak to your interactions with Apple Support. I don't know what they were looking at. For one thing, it's rare that anyone ever looks at permissions, so I could totally understand if they didn't know anything. They're just tech support, after all. On the other hand, in your post after having upgraded to Sonoma, your data looks much more interesting. So I don't know if you were talking to support about the read-only system files, which is totally normally and expected, or your funky permissions on user files, which are not normal at all.
4) Normally, when looking at permissions for things like Desktop, Documents, Movies, and Pictures, you do have read and write access. Furthermore, you are identified. It should say "admin (Me)" with read and write permissions. It also shouldn't list "system" at all for these files. Your entire permissions are totally scrambled. So that's what's going on.
And that brings me back around to this "maintaining" that you mentioned. Are you running any kind of "clean up", "maintenance", "app zapper", system modification, system hack, or "security" apps of any kind? I mean anything? If so, that's the most likely cause. Had you enabled the "root" user at any point? That might do it too.
Regardless, there is no point in wasting time with it anymore. Erase the hard drive and reinstall the operating system. I don't know if your backup can be trusted. You'll have to recover your data files from backup manually. When you copy them back over, they should have the correct permissions. For other, database things like Mail, etc. you'll have to resync from the internet. In the future, I strongly recommend iCloud for syncing files. Time Machine is great for backup, but if you really scramble your system like this, then your backup will be scrambled too. In these cases, and for a few other reasons, iCloud is actually better than Time Machine any time there are mysterious problems like this. Time Machine works great, but it will backup problems along with everything else.
And lastly, never ever assume that an upgrade is going to magically fix any problem. That never happens. It will only cause new ones. If your current system is working great, then there is really no need to upgrade. If you have problems, upgrades will only make your problems worse. But if your current system is working great, and there are some neat new features in Sonoma that you really want, then by all means, do the upgrade. But even in this case, I don't recommend being an early adopter. It will be a non-stop exercise of updates until macOS 15 is released.