Hi Amiga2000,
Try a program called 'AutoUpdateWB' (Probably on AmiNet).
This automatically updated without having to press anything. The only thing it doesn't seem to do is update png icons:
For example when you rename disk.png to disk.info.
In that case you have to close the window then reopen it to see the icon. Every other update is auto, even if you copy/delete etc in CLI.
FuZion.
BTW, @ Hyperion is this feature in OS4 or will we need a program like this?