Syncing all your stuff between all your digital devices is going to eventually drive you insane. Apple is here, once again, to help. iCloud (Free/$25 a year) seamlessly stores your music, photos, apps, email, calendars, and documents, and wirelessly pushes them to all your devices automatically so everything stays up to date and in sync. When something changes on one of your devices, all of your others are wirelessly updated almost instantly. You can also use iTunes Match to have all of your ripped music available to you on any device for a yearly fee. You've been hearing about this "cloud" stuff on crappy IBM commercials for a year, but now (well, this fall when iOS 5 is released) you'll actually benefit from it.