The entire Windows 9x line was fine in its time, but its time has passed. Its basic architecture, with little tiny memory heaps for handling system resources, means that every member of the Windows 9X family is inherently unstable. And although its insecurities could probably be repaired, the cost of doing so would be to break many applications.
It’s ironic that Microsoft in those heady pre-Y2K days was on a fairly consistent annual upgrade cycle for Windows. Windows 98 in 1998, Windows 98 Second Edition in 1999, the forgettable Windows Me in 2000. Each one was a paid upgrade (although some features from Windows 98 Second Edition were available on CD). On the other hand, if you bought Windows XP in 2001, you’ve received one major update and a gazillion tiny ones for free.
To celebrate the demise of Windows 9x, Brian Krebs of the Washington Post put together a list of “security tools that still play nice” with those outdated Windows versions. It’s a good piece of work for those who absolutely insist on continuing to use an unsupported OS. Personally, I think all the vigilance that strategy requires is a waste of energy. If you have a 1998-vintage (or later) CPU and at least 256MB of RAM, you can run Windows XP with acceptable performance. Windows 2000 uses even fewer resources, doesn't require product activation, and provides a level of stability and security that is infinitely better than anything in the 9x family. If even Windows 2000 won’t run, it’s time to retire that hardware.
Buh-bye, Windows 98. We really won't miss you.