I own an iPod. Proudly. Not to be hip or wear white headphones because I dont. I use it primarily for in my car. In combination with the iTrip Nano from Griffin, I use it to listen to my MP3's and podcasts. "Look ma, no headphones". And I like my iPod a lot, in fact one wonders why not every remote control (for TV or radio/cd) does have the userinterface of the iPod.

I wish I could say the same about iTunes; the application to sync your playlists, photo's and podcasts with your iPod. But I cant! It must be the worst Big Application I have seen on Windows, ever! It is wrong in so many ways I cant even sum them up all but let me try to give some points why iTunes sucks:

1. Crash. I work in a datacentre where lot of sensitive data (think all governmental data of all the inhabitants of The Netherlands are stored but also the root certificate of the Dutch state and via a special operations network ways to maintain dozen of applications and hosts including the biggest media sites in the Netherlands). So we have to lock our workspace when we are not at our desk. That and the fact that if you dont, your cow-workers will put "special images" as your background, send out mail to people via your account or do a software rotate on your desktop and disable the ability to undo this via a shortcut. So I lock my desktop. But if iTunes is fullscreen-ed when locking... it crashes. Badly! why? I dont know but it sucks.
2. Userinterface. I understand that for Apple the iPod is the best way to push Mac's to windows users so they can switch. So they want to have their imago ("the aqua theme" look). But forcing this apple look including close buttons and other user interface elements on every Windows user sucks. You should never ever change the way the user knows how to work with his system. Only very immature applications mimic other UI's, all applications that respect the user more then the will of the vendor, will use the UI the user has chosen, not the vendor of the application. This is really a big usability booboo and Apple should know better!
3. Syncing with local storage. This is the most stupidest thing I have seen. You can select a directory with MP3's to be indexed and everything is voodoo magic from there, great for the users, right? Wrong! I had some 40GB's of MP3's locally on my laptop and iTunes indexed it fine. But then I decided to use a central Samba repository for my MP3's; a server at home so I can sync with other PC's as well and use the MP3's as well for my Squeezebox. Believe it or not, you can ADD other directorys to be indexed, but you cant (CANT!) DELETE a directory to be indexed! The only solution is to delete the directory from the filesystem and start from scratch. I did. Now iTunes has all the MP3's listed twice and hence iTunes cant find half of the songs. You *can* tell iTunes PER SONG where it can be found if the file has been moved. But you honestly expect me to point 40GB's of MP3's manually to the new directory? Boy, is this how all Apple software's logic work? Because if that is the case, I'll rather switch to Ubuntu then to some braindead OS.
4. iTunes account. iTunes has some kind of internal browser to browse the iTunes store. It is just HTML flying around, including GET's and POST's. And if you want to buy songs or games (hey, testris on iPod seemed cool!), or get some album covers, you need an iTunes account, the .Mac people have this by default. But not the Windows losers.. So you would think you can create an iTunes account in the iTunes application for the iTunes store, right? Wrong! When you use a function that requires an iTunes account, you are not directed to a page where you can create one, there is not browser starting pointing you to the iTunes site, there is no useful error. No, you get a "create an iTunes account on the Apple site" error. Ooooh, how helpful, thank you for that. Now I dare you, count the mouseclicks it takes you to find the place where you can create an iTunes account. I am rather Google savvy, but I spend more then a couple of minutes finding the place. .... Found it yet? ...... Honest, every music piece is within reach with 4 iPod clicks, but creating an iTunes account will be at least 10 times as many clicks, wasnt it?

And this is just a start, I can go on and on. iTunes on Windows as an application sucks, no matter how much "wet floor effects" they add to the userinterface.

But lets end this posting positive. My daughter Brecht loves the iPod, "waar is ipot nouw?" ("where is the ipod now?"). Especially since I use it as a remote control in combination with the iTrip for my stereo at home. See even "gets" the UI, the best way to test if the UI is good is to let it be used by a 2.5 years old. However, the first time I showed how to use the device, she said "waar is knopju nouw?" ("where is the button now?"). 2.5 years old and already legacy (missing button) in her head, that is weird. But also, 2.5 years old and the legacy (missing button) is whipped away in a second.