First off, congratulations. You will love that unit.

Buuuuttt, if this is your first Apple product, your above statement leads me to think that you are in that "Windows, let's try to do it the hard way" way of thinking. iTunes sync could not be any simpler - just plug in the cable. My recently purchased Droid requires manual drag-n-drop transfer of files with the computer's file manager - the one thing I really dislike about the phone.

iTunes works great for media. If you want to upload Office files, there are several apps that allow syncing over your wireless network and don't require the cable. MobileMe service also has an "Air disk" that works that way. I believe that Dropbox also has an iPhone app that would sync files automatically between the phone and computer(s).

As for the GPS / battery life issue - my Droid batt. drains pretty fast when using GPS apps too. I think that is just the nature of these things. I'm sure technology will eventually overcome it with better batteries or more efficient GPS chips, but in the meantime, keep the power cord handy. There are lots of cigarette lighter plugs with USB ports that you can purchase for vehicles, combine, tractors - keep the unit plugged in as much as possible and use the GPS all you want.