That's probably a fair point. I can't say too much as I haven't touched Windows desktop or server too much.
Could be apples vs oranges here though as we're talking about getting started versus well established setup, but my current employer is looking at adopting Ansible + Packer for imaging and partially Ansible-managing Windows servers where it makes sense because of limitations in SCCM and GPO. As far as I can see across the divide Windows Server isn't all smooth sailing.
Yeah it is a bit of a pain. I currently only have a few users. Tooling-wise there are ways to tail the journals (if you're using journalctl) and collate them but I haven't gotten around to doing this myself yet.