I like to define a five-point touch system for my database upgrades. If the new version doesn't change my life in five ways, then it's not a significant upgrade. I'll typically quantify my need by approximating how many hours I spend each week performing certain tasks, and then estimate how much time the upgrade will save me. If I spend five hours every week dealing with resource usage and the new release will do it automatically, then I figure the upgrade will save me five hours a week. Now all I have to do is quantify four other features the same way, and I can sell it to management.
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