My immediate family owns an iPod Mini, an iPod Nano, a video iPod, an iPod Touch and an iPhone. And two PowerBooks. And a Mac Mini. And a Lisa. And an Apple I. And an Apple II. I became an Apple developer in the early 80s on the Apple II, and was a Mac developer for 12 years. Loyal? I was also a Newton developer.

Enough about me. I am so fed up with Apple. They are tragically uncool. My iPhone experience has been a nightmare. First, no one can activate it for you. You activate it from iTunes. But you have to have the right version of iTunes. To get the right version of iTunes you need the right version of Mac OS X, 10.5. If you don’t have it, it will cost you about $139.

So I updated my OS to 10.5. Guess what that did to most of my Macromedia graphics apps and PowerPoint? Yep. They don’t work anymore. Adobe Fireworks is available from Amazon for $297.99, $1.01 off of list! Mac Office 8 upgrade? $240.

Estimating conservatively, I have spent close to a million dollars over the years on Macs, Apple laser printers, CD ROM drives, software, etc. I ran my own business and we both developed Mac peripherals and software and bravely ran the company on Macs. I’m not talking about managing some corporate budget worth close to $1M and spending it on Macs. I was an entrepreneur. This was money out of my own pocket. But I digress.

In addition to a couple of thousand dollars in recent investments in iPods and the iPhone, I HAVE PURCHASED LEGITIMATELY THROUGH ITUNES several hundred songs. Great stuff. Buzzcocks. Clash. Snow Patrol. Bummer I can’t put them on my iPhone. That’s because Apple forces people to update iTunes so they can introduce hardened and more insidious digital rights management (DRM). DRM is designed to keep people from playing music they have legitimately obtained. You thought it was designed to thwart music theft? No way.

Last week I heard 27 Jennifers by Mike Doughty and I loved it. I came right home to buy it from iTunes and put it on my iPhone. I paid my .99 and downloaded it. I connected my iPhone and tried to sync it. (I have yet to get the calendar to sync). I was alerted to the fact that I needed to update the iPhone software. I downloaded it. I then updated the iPhone which took a LONG time. It also failed to install the update. I tried several times with repeated failure.

I also could not get 27 Jennifers or any of my purchased tunes onto the iPhone.

So tonight, I fixed it, or at least, I got 27 Jennifers onto it. I booted LimeWire, searched on the title of the song, found it in 10 seconds, downloaded it in under a minute, dragged it to my iPod and iPhone and guess what? I can finally listen to the god damn song I bought a week ago.

Apple … what is THAT all about? With the cost of the phone, the tunes I can’t play because of your hideous DRM, the OS upgrade, and all the apps that broke with the upgrade, I had to spend $1000 JUST TO GET MY IPHONE, MAKE MY FIRST CALL, AND RESTORE THE APPS THAT BROKE IN THE PROCESS!

Steve Jobs came out in February of last year and said he opposed DRM. What does that mean? The DRM that plagues iTunes and the iPhone must be the most onerous ever. Jobs explains Apple’s DRM policy in an elucidating 1800-word plus Thoughts on Music on Apple’s site. Despite the title, it is not about music. It’s really Thoughts on Greed. There’s not a word about musical genres, the joy of good music, the artistic experience. It’s an explanation of why iTunes music has to carry DRM even though Steve doesn’t want it. (He would also prefer to give away all of the company’s products, but that decision is ultimately up to the Board.) Jobs writes “all iPods play music that is free of any DRM.” A friend of mine told me, never buy your music from iTunes and you won’t have a problem. I guess that’s the answer.

I know this is a story that has been told thousands of times, but it’s infuriating, and it’s my blog, so there.