How can I set up a report or notification to let me know if the computer hasn’t been updated with windows or a third-party app in the last “X” days?
Here’s what I have for monitoring Windows Updates. You can configure how you like but currently it alerts on EOL builds and lack of a cumulative/rollup update in the last 50 days.
Third party is more complicated. Syncro of course can update many apps automatically via chocolatey if you set it up. There’s not an easy way to monitor if all apps are on their current versions though. You can do saved asset search for a program and version number below x but that’s very manual. I’ve got a rough check script made up for alerting when chocolatey updates fail, but that’s not exactly what you’re wanting either.