The aspect of upgrading windows, only looks for a previous installation of any version of windows, it doesn't matter if it's activated or not, as it has no way of verifying that kind of information. It sees C:\windows\system32 and such and says OK, I can install now. So the easiest OS to upgrade from, is merely an unactivated version of the same OS you are using. You can't switch between 32 and 64 bit, and you can't downgrade from Home Premium to Home, or Ultimate to Home Premium, etc, it always has to be the same or "greater" version. I have only done this with Vista, as I had purchased windows 7 ultimate upgrade versions, but with windows 7 I have OEM full retail versions, but the process should be the same.
Even if you do have to install XP first, it's not a big deal, and you don't have to worry about xp having no knowledge of how to utilize an SSD, as the xp files will get moved into a windows.old folder, and will no longer be bootable.
You can image to your heart's content as far as my experience tells me. I don't think a hard drive swap will flag windows to reactivate, I believe that's reserved for bigger things such as motherboard swaps.
Here's some more info
http://www.maximumpc.com/article/how..._disk_fresh_pc
http://www.mydigitallife.info/clean-...nk-hard-drive/
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