The only AV I use is MSSE. Do I really need to uninstall it?
If you mean the AV built into Windows 8/8.1 (Windows Defender) then you can leave it be (you can't uninstall it regardless). If you mean Microsoft Security Essentials that you've installed into Windows 7, then yes you should uninstall it. MSE/MSSE generally behaves okay with Sysprep, but I just wouldn't risk it.
I've also never heard of OOBE, so I googled it. Sounds like OOBE basically lets you cutomize the Windows setup experience after you've run sysprep. Is OOBE part of sysprep or a seperate utility you need to run?
OoBE is the Out of Box Experience. It has to be run in this context. In a corporate environment you would include an answer file to prevent the end users from seeing the OoBE. For this situation there's little point to that kind of work.
As I recall, upon first boot after sysprep, Windows configures the machine as if it was a new install, letting you rename it, etc. Will sysprep keep all my user settings intact?
You've just described OoBE.
Your user profiles and application will be left unharmed, but there will be a few system settings that have to be redone. It's a painless process.
All sysprep is going to do is eject all the hardware specific information from the system. This returns the OS to a clean slate giving you a fresh install on the new hardware.
Oh, and I do have full backups already courtesy of my Windows Home Server 2011.
Excellent. Contingencies are a must.
Thanks for the advice on sysprep, I hadn't thought of using that. I've used sysprep in the past with Windows XP on corporate workstations, but not on anything newer than that. I'm sure sysprep has only gotten better.
Combined with Vista and newer it's pretty amazing. IT asked for better imaging capabilities and Microsoft modified the guts of the OS to deliver.
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