Windows updates will be one thing I won't be missing, because they've indeed brought more trouble than they are worth. My main Windows XP SP1 system installed in 2008 is still working well. It was originally installed on an USB drive with some modifications, and then transferred. After I upgraded my processor, I never re-installed, but merely changed the HAL.
Updates needlessly interfere with a working system. Occasionally they need research and advanced knowledge (more than I have). Some things that come to mind: tcpip.sys with the imposed half-open limit (before you think P2P, it's enough to transfer "small" files over FTP to set it off), unstable network adapter drivers pulled from Windows Update, installation of unneeded IPv6 which interferes with local DNS resolution, the Event Log filled with messages from HHCTRL every time a CHM file is browsed (by the time I trust a CHM file, I've trusted the exe it came with already).
I just faced all these isues when dealing with this SP3 PC here.
I'm sometimes in an online chat and the other party is telling me that they'll go for a reboot, because a batch of Windows Updates are demanding so. That's completely unacceptable to have my PC hostage, and rebooting at somebodys else's request. (I think there is probably a choice to postpone it, but even so.)
I see these very chatty updates a method to pre-condition users into thinking they can't survive without them.
My PC is also behind a router, and has always been.
I have not done it, but will when I do upgrade, but if you create a separate partition for your home directory, you supposedly have a much easier time upgrading as all your settings are saved in your home directory. We have all done the somewhat the same thing with Windows, by installing the OS in a partition and then putting all the data on different partition.
I agree that this is the right setup, and I implement it on all my PC installations. It helps if the OS is reinstalled. But it hardly helps in updating, because every new Windows version is taking up more or much more space. The bigger is better. If the System partition would fit a new OS, the hard drive wasn't used efficiently before. My Win98 partition: 1 GB (Win2k would fit there), WinXP - between 3 GB and 8 GB. No way to put Vista on there.
When talking about "upgrading" instead of reinstalling, apparently NT 6.3 upgrade installer doesn't "support
" such a customized system at all.