I don't work for Linode, but I can answer some of these:
(1) I have no idea, sorry.
(2) It is done on the fly. You do need to reboot to see the new hard drive space/memory, but DNS doesn't have to be updated.
(3) Backup is currently in beta, but you can sign up by opening a ticket. It is automatically done on a daily basis (snapshots) and weekly basis (full). You can restore from any of the snapshots at any time.
(4) and (5) Linode is completely un-managed. You have to provide your own expertise and handle the move/maintenance of the server on your own. Honestly, if you're completely unfamiliar with Linux management I would recommend you either hire someone to handle the switchover for you. IMO, there's just no way you can learn all you will need to know in order to successfully administer the server in the time frame you're looking at.
edit: I should mention, Linode support is excellent, and they will help you if you have specific questions. They also provide
excellent documentation and
tools to help you get the work done, but with a site that big, the little experience you say you have, and your time constraints, I think it's just not something you can tackle on your own.