stevec
For # 2 I plan to try this: http://www.xlnaudio.com/support-knowledge_base-offline_installation_of_addictive_keys
It's not written for AD, but the process looks like it might work.
I don't think you got a chance ...
I have installed AD on one DAW via the online installation process. It did not ask for any paths (which is annoying) and it also immediately deleted all downloaded packages, so that you could not transfer this anywhere else (which was major annoying as I did not want to do another 1+ GB download via mobile networks).
So I transferred all AD files I could find on DAW #1 to DAW #2 and - hurray - you get a fully working version of AD!
BUT, of course, it is only a 10 day demo with a dialog box explaining how to do the offline registration / activation. When you follow these instruction, you'll realize that they removed all offline activation functionality from their webpage i.e. there is no way to do it.
So you have to get online to activate, but at least here it is quick as the installer does not need any further updates and AD itself only needs to repair 2 dlls to be ready to go.