I've examined the profile migration tools for Windows 2000 and XP
(they're part of the Resource Kit, not built-in, in Windows 2000 BTW). 
The problem is that they only store off the settings for the
applications they know about (basically, Microsoft applications, and a
few of their good friends).  They don't even store all of the settings
for the applications that are handled, only the ones Microsoft
determined are "important".  I'm not saying these tools aren't valuable,
only that even an experienced, knowledgeable, careful, and well-prepared
user can have issues with an upgrade on a Windows platform, and an
upgrade on a GNU/Linux platform is (IMHO) considerably smoother due to
the basic design of the system.  That same design can lead to serious
problems on GNU/Linux at times, but it sure makes an upgrade easier.

Roaming profiles are great, if you never use 2 computers at once (ask me
about it sometime), have an ActiveDirectory domain controller, have
system admins willing to allow it (most won't), have the network
bandwidth to support it, have a network server with enough space for all
of the profiles, etc...  Many business users, and nearly all home users,
don't have what it takes to select this option, and roaming profiles
don't actually work after an upgrade, the system won't accept the
registry hive, because it's not for the same Windows version, so the
user still has to redo all their preferences (or everything the profile
migration tool didn't handle, at least).

I'm not a Linux expert, yet, but I've had a bit of experience with
Windows system administration over the years, and, so far, I've found
Linux systems deal with upgrades/reinstalls/etc... better than Windows. 
Windows still wins on ease of use and is way ahead on ease of
administration, but the gap is closing in those areas, which is why I
was finally able to switch to a GNU/Linux system for day-to-day home use
(although some tasks still require Windows, mostly due to software with
no Linux-compatible equivalent and, thankfully rare, websites that
utterly fail to work in any browser except IE).

==Joseph++

Craig White wrote:

>----
>actually - it can but you have to be knowledgeable and deliberate - two
>things that most Windows users won't do and of course, have the presence
>to create the separate partition for the data files - which isn't
>possible the way Windows is distributed by the vendors - at least not
>without some major steps of partition alteration or reformatting and
>starting over. Thus after you solve the partition issues...
>
>There are profile migration tools both built in to Windows NT-2K-XP and
>available separately and of course, you can always do some registry
>editing to redirect the specific user profile elements (My Documents
>and/or Favorites/Application Data/Desktop etc.)
>
>Then of course, there is always the option of creating a windows domain
>- where the profiles roam and are backed up on the server thus you can
>delete, reformat, upgrade or add another computer to the mix and your
>user settings will follow you automatically.
>
>All in all, Windows scores pretty well on this topic so I would
>generally disagree with Josephs assertions about Windows not handling
>this well...it just doesn't handle it well for unknowledgeable users.
>
>Now - as for Linux upgrades...I have had problems migrating to newer
>releases on the following (i.e. - retaining $HOME directories through
>and upgrade):
>- openoffice.org
>- gnome
>- kde
>- mozilla
>
>and probably some others - but it is relatively simple to...
>cd $HOME
>mv .mozilla .mozilla.bak
>then launch mozilla and finally quit it again and manually move my
>bookmarks etc. from the .mozilla.bak subdirectory to the .mozilla
>subdirectory.
>
>Craig
>
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