No, you do not need to upgrade to server first. You can go straight from 4 WKS to 2000 SVR.
One part that is a slight gotcha is the NTFS converstion - your existing NTFS partition must be converted to use NTFS5 to work, and this was a lengthy process the one time I had to do it.
Honestly the best method is to install cleanly if it's at all feasible. Upgrades will work on clean partitions - simply have the prior version CD handy when it does its check. Switch the CD when prompted, and switch back again after it's done checking.
Doing this will also allow you to customize your setup and give you more flexibility. It eliminates a LOT of the hassle of uninstalling applications that "may or may not work", as well as having a bunch of icons that when clicked give you warning msgs about running under W2K and have been disabled.
Back up EVERYTHING before you start - regardless of which way you choose to do this it's a one-way-ticket. There is no uninstall path except for "restore from backup"
Norton Ghost and PowerQuest DriveImage are both suited to this task. Professional/Enterprise versions allow you to transport images across network segments for remote storage in LAN environments. They also allow restoral over those sane networks
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