This was a tough one for me to answer because I don't really buy new computers, just upgrade mine all the time. But usually if my friends have a better system then me (none of which are techies like my self) I know it is time to upgrade.
I upgrade when I build for friends/family. They usually want something around the range that I have, so I use that for them and buy new for me. Works for both of us.
I think you need to add an option about reliability. I upgrade my components when I can no longer trust them. That's why my HD and sound card are both being replaced soon.
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