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To upgrade a Windows 3.x machine, think carefully. Check Chapter 3 for hardware requirements for Windows 2000 Professional. Assuming the machine can cut the mustard, you can do the following:
Upgrade to Windows 95 or 98.
Try to get everything working correctly before moving ahead, but if you can't get a piece of hardware to work, don't fret. The upgrade to Windows 2000 Professional might solve the problem.
After you have successfully upgraded to 9x, do the upgrade to Windows 2000 Professional.
Use the system troubleshooters in Windows 2000 Professional to solve driver and hardware problems if devices are not working properly after the installation.