Microsoft Windows 98

Release date: June 1998
Initial price: $109

Reader RobBob believes incremental upgrades of Microsoft's flagship operating system in the past several years haven't improved the user experience much. "When I realized, many years ago, how the computer industry's incessant but marginal upgrades were really designed to rip me off, it became a point of pride to see how long I could keep legacy machines, OSs, and apps running productively," he writes. "I only had to upgrade recently because my two Windows 98 machines died of old age."

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