[aiharkness]

You will be able to upgrade to the latest OS, assuming it isn't already running it, but checking for updates is an automatic part of the setup procedure. How easy it is depends on you. I think it is easy, most people think it is easy, I believe, but there are still some who struggle, as is always the case no matter what. If it is a wifi version of the PlayBook make sure you have wifi available before you start the setup.

You will not be able to move files directly between the PlayBook and the BlackBerry handset, unless there is an app that does this, which I don't know about. I really doubt there could be anyway to put saved messages from the handset on the PlayBook. But stock out of the box you will be able to access files that are on the BlackBerry handset when bridge. And you can use either the onboard email app or the bridge email app.
Posted via BlackBerryForums.com Mobile