My gut reaction to "menus that learn" and "rearrange themselves" was NO WAY FORGET IT because it would be counter intuitive. However, my office has switched over to Windows 2000 and the start menu is a "menu that learns" and eliminates items that are not frequently used into a ">>" (or "..." in other words). So frequently used items bubble up and infrequently used items are summarized away and this amazingly cleans up the menus incredibly! And it's not as unintuitive as I originally thought.

Later on, I noticed that some of the more prominent web sites have rudimentary order by use features and remove by disuse as well.

So I'd say, yeah, definitely implement a learning menus feature. Just make sure it can be disabled for the "power" users that click through the menus without looking.

Calvin