On one hand yes but then again, those lucky enough to be swapping computers regularly are suffering from first world problems. ;) I don't use iTunes but I love having an MP3 player vs disks. Remember accidentally dropping your favorite CD in the car and it getting a nasty scratch which caused your finicky CD player to either skip three tracks or just get stuck trying to read the disk for twenty minutes before spitting it out like the tongue of an unruly child? I'd take having to re-download my favorite tracks, taking five minutes of trouble, than having to buy a whole new CD because the car ate mine.
Outlook? Dump that dinosaur and put all your contacts into gmail. That way no matter where you are, you have access to all your information, and you can avoid the "I'm updating and need to drag another thing with me to my new rig". It's all online and backed up.
Movies. I'll give you that one. I prefer knowing I'll have access to favorites whenever I want and online services perticular quirk of "rotating" stock is annoying. So I keep DVD's of my favorites, of which I have few, but I wouldn't give up hulu or netflix to go back to only having DVD options. In 2012 it's nice to be able to use either or instead of being forced to get everything on disk, and spending a fortune to do it.
As for photos, consolidate, consolidate, consolidate. Create a central media server that's for nothing but music and photos. Shove a couple terabyte drives into it and then, since it's just acting like a server on your network, anyone in the house can access the central digital music library and photo archives no matter how many computers they upgrade to. Don't blame the technology of the day for your lack of imagination. ;) I'd take this way of doing things over having to find space to store all those old photo albums that are a pain to dig out and look at, instead of being able to check out your stuff on a whim with a click of a button.
Also, do you remember how bad taking photos were before the digital revolution? It really was an art form, and not many of us were skilled photographers. You buy a roll of film, point, and shoot with no little screen to show you sort of what it was going to look like. Then you had to pay a hefty fee to get them processed only to find out half of them were blurry and the other half were overexposed. You'll never be able to go back to retake those shots so the event is lost forever! With digital you can see what the shot looks like right away! Toss it and make people sit still for another one until you finally get the one you want. You can take a zillion shots on multiple little memory cards and then pay nothing to put them onto your computer and tweak them to your hearts content, picking only the best of the bunch to save. I wouldn't go back to the old way of taking pictures because, well, I really really sucked taking good photos with pre digital cameras.
I have all my photos consolidated into one large, very organised system and I've taken the choicest shots and created various "albums" on facebook. And if I want to move them somewhere, facebook has an "export album" button that will dump all the photos, captions and all into a file to be imported elsewhere.
If you're feeling disheveled in this digital age, it's time to get organized! Start with a central server for the home. It's a gift that keeps on giving and a great asset when so much of our lives have evolved away from an analog world.