A)
From experience, what you're looking to do isn't possible. I've tweaked my imaging process to the best of my ability, and I have emergency deployment times down to 6hrs. (Which is the time needed to encrypt a laptop.) Imaging solutions generally overwrite any data currently on the hdd before encryption. So I don't necessarily see away around this.
Maybe if you were using a scripting approach for imaging then I'd assume it would be possible in a way. You could in theory encrypt all of the laptops beforehand, and use the unattended.xml file to script the rest whats needed before deployment. On the downside, cleaning up the records on the server would become a little tedious.
Would love to hear feedback from others on this though as I could be missing something.