"Taking risk" button

When working with Windows, you often do things which you haven't done before, and are not completely sure about. The common practice when doing such things is to save backups of data and use "undo's" for backtracking. The problem becomes more complicated when you are not aware of all the possible consequences of your action and therefore you rely on the system backtracking capabilities. In XP for example there is the "Last known good configuration" which helps you recover from system boot failure.

What I'm suggesting here, is a "taking risk" mode, which tells the system or any application to take extra care about the activity, and to enhance the logging and reporting of what went on since entering that mode.

My feeling is that keeping a uniform level of "undo" possibilities takes alot of resources on one hand, and doesn't always help you when you really need it, on the other.