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The upgrade process is, as everyone in the Technology-related press certainly seems to believe, straight-forward and generally painless. Unless the hardware your PC or laptop has is not compatible or the related drivers are not quite "mature" enough just yet, you will be able to upgrade.
Don't assume every piece of software being used on the current Windows 98 system is compatible with the Windows 2000 architecture. Some software you have will most likely not be usable in Windows 2000. You may need to upgrade that incompatible software (read: pay $$), and at the very least update the drivers for some hardware. Per usual, preparation is the key (oh no, I sound like my 9th grade English teacher).FIRST: Microsoft Windows 2K Upgrade from Windows 98: do a THOROUGH backup of each and every folder and/or file you consider precious.

The upgrade process itself is not too difficult. The challenge is reviewing the software you have installed and finding which is compatible/not with Windows 2000 Professional. Also, do the same with your hardware. Don't assume that the video card you currently have working so smoothly under Windows 98 will perform the same under Windows 2000 Pro. Do some research before jumping in. The research is probably the most challenging part of the upgrade process, believe it or not. Once you are comfortable that your hardware and software is compatible (or you can do without incompatible software until you upgrade to a "Windows 2000-compatible" version"), then you move on to the simple step-by-step instructions below.

Research begins here:

Preliminary Steps:

Article ID: Q256070: Microsoft's advice and general 2 cents on upgrading:

"FAQs and Highlights for Windows 2000". Covers both W2000 Professional & Server.

NOTE: there are issues with Dual Boots! Try Article ID: Q23212. Also, although MS doesn't mention it, if Linux (or Unix cousin) is installed on another partition and LILO is boss, kiss LILO goodbye.

MS Readiness Analyzer Knowledge Base Article

http://support.microsoft.com/support/kb/articles/Q253/7/71.ASP

** It appears the MS "Readiness Analyzer" tool is currently not available form the web site

http://www.microsoft.com/windows2000/server/howtobuy/upgrading/compat/ready.asp: try it anyhoo....[you'll get the 2 links below as of 8/01]

Also, there is a Readiness Tool available on the Windows 2000 CD, but I would manually search the databases mentioned below on the MS web pages: it is best to simply check this way. Enter the software or hardware you need to check, etc. Most, although certainly not all software and hardware today is compatible with the Windows 2000 architecture. Be especially careful of any smallish freeware or shareware software! Also, watch out for software versions you have had installed for more than 1-2 years (i.e pre-2000).

Hardware Compatibility:

http://www.microsoft.com/windows2000/server/howtobuy/upgrading/compat/search/devices.asp

Software Compatibility:

http://www.microsoft.com/windows2000/server/howtobuy/upgrading/compat/search/software.asp

**** Onward toPart 2:

Step-By-Step Upgrade with images