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I think Microsoft tried that with Office (2000 and more ?), they had adaptative menus. Apprently most of the users disliked this feature and it was eventually removed (http://blogs.msdn.com/b/jensenh/archive/2006/03/31/565877.as...)

They did, and it worked great on your own machine after a few weeks. The problem was it made everyone else's machines basically unusable.

Good idea, but there would have to be cheats, be it for urgent tasks or because of a reinstall.

Wow. This is bikeshedding to the extreme.

Or a programming language. We can measure 'level' in pointers. Then we'd have a practical application of the term 'three star programmer.'