As far as constant rebooting, I have encountered this, however I never troubleshot the problem, I just reverted to a previous snapshot and attempted to sysprep a little differently.
I have run into problems with the windows error reporting before the OS boots, but again, I just reverted to a previous snapshot and worked out the kinks.
[quote]Okay, so I read more and figured out that sysprep does what I need it to do. Questions though:
1.) What is sysprep actually doing?
2.) Can I only use it a max of 3 times?[/quote]
Sysprep releases the OS from the specifics of the hardware and thus allows it to be installed on another machine.
Sysprep takes care of all the mess of changing/deleting the registry values, and it allows the new hardware to write it’s ID information to the OS and will allow the OS to be activated.
KMS servers have to have a unique ID for each machine that wants to activate.
I do my sysprep process in a virtual environment and this will leave it open to any type of hardware, so long as I supply the drivers (i do so in the os and reference to them later with registry values). However you can also install the OS on a hardware to install updates, programs, etc then audit. After you update the Windows installation, at the command line run the Sysprep /audit /generalize /shutdown command to configure Windows to boot the computer to audit mode. You can then capture the Windows image.
Use the new model-specific reference image to install Windows on a new computer. The Windows image is applied to the computer, and Windows boots to audit mode.
(Optional) You can install additional applications and other updates. You can also test the computer to verify that all components are working correctly.
After you update the Windows installation, run the Sysprep /oobe /shutdown command.
NOTE
If you install Windows images by using the Sysprep /generalize /oobe command, the user experience will not be ideal. On the next reboot after you run the Sysprep /generalize /oobe command, Windows runs the specialize configuration pass, Plug and Play, and other Setup tasks before Windows starts OOBE. This process can take additional time and can delay a customer’s first logon.
To answer your second question, YES you can sysprep more than three times.
One option is to use the Virtual setup I talked about and use snapshots to revert to a time before sysprep has been ran and update/push again.
OR
During the set up of your unattend.xml file you can skip re-arming the os and this THEORETICALLY gives the os 999 re-arms, it should be noted that this is heavily frowned upon and I highly recommend the virtual set up. Snapshot can save you a LOAD of time if you don’t have to re-set up the OS and install the damn updates again!
If you would like, I have a word document I have been using to keep track of my sysprep adventures, it would give you a good base to work from, and it is set up in a walkthrough style.