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automate installation
"7. Rebuilding and installing Windows.... endless updates and reboots required"
If you're doing this more than once or twice, you should slipstream all the current updates.
See for instance the "Unattended Windows" forum at http://www.msfn.org/board/forums.html
There are several projects discussed there (eg, HFSlip, nLite, vLite) that can automate the building of a up-to-the-minute installer and give you a one-click install. (This is entirely legal, BTW.)