Tesla does rolling software updates. Best thing you can do is leave the setting on Advanced, there's simply no way to force an update even if a newer version has released and others have gotten it. You will receive the update once its your VIN's turn in line, sooner than others if you opt for Advanced over Standard. If there is a newer software version out and your car says "Up to date" it just means it's not yet available for your car configuration/region.
Per Tesla's website:
When do software updates become available?
Software updates occur on a rolling basis. Tesla will notify you through an alert on your car’s touchscreen and Tesla app. To see if your car is up for an update, tap 'Controls' > 'Software.’ Your car will check for updates and display “Checking for updates..”