When? At home, it's usually very soon after I have come very close to requiring a new machine due to putting my fist through the screen. Then I think to myself: "Self, maybe it's time to rebuild this bad boy". And then I give the machine to somebody and buy a new one, since I'm too lazy to reformat it and I really need something state-of-the-art to surf the web with.
At work, Acronis images save the day. 1. Get new hardware. 2. Install your crap. 3. Image it. After six months, slap a new image on it, just because it's taking twelve seconds longer to start up than it used to.
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