Not too long ago, I wanted to be an Apple fanboy quite badly. I had this little device known as the iPhone, which connected me to the Internet when I wasn’t at home, played music, and reputedly could even make and receive telephone calls.

I loved that iPhone.

And it connected to my computer with a little special cable, where an Apple program called iTunes would synchronize it. iTunes held — and still holds — my entire music collection.

Then things started getting sour.

It began even while I was still in love. Apple wouldn’t let me just turn on my own fucking phone that I had just bought. No. I had to wait until I was home, install iTunes and perform an initial synchronization.

And they wouldn’t let me just install iTunes. They had to try to add their MobileMe service (and later their Safari browser). And not just the first time – they would ask me with every iTunes upgrade that would ever come out.

And they wouldn’t let me put whatever I wanted on my phone. Only specially-approved-by-Apple software could go on a device that I paid hundreds of pounds for.

But I didn’t care. My iPhone was so shiny.

It turned out, however, that these were not glitches in the Apple paradigm; these were instead indicative of Apple’s approach to doing business. And as Apple continued down this road, I decided to stop supporting them with my money. I would cut them out of my life, hardware and software alike. For Steve Jobs & Co., there was no more time, money, or space (real or virtual) in my life.

The iPhone was dutifully ditched for an Android, and this blogger has not looked back. (Well, he has, but he’s had a big grin on his face about the decision.) My other piece of Apple hardware — an external hard drive — was given away.

But there remains one problem: iTunes.

Unbelievably, it remains on my computer — I use a wonderful program called iSyncr to synchronize my iTunes playlists with my Android phone. It works wonderfully, this system of mine. Except that it keeps Apple software on my computer.

And I desperately want to be free of Apple software.

At first I went to DoubleTwist, which is billed in every corner of the Internet as a “must have” Android app, and the Android version of iTunes. It was awful.

Cory Doctorow wrote on BoingBoing about Miro, so I gave that a try. Not only did it lack the functionality I hoped for, but Miro is additionally so full of advertising (and so pushy about its advertising/requests for donation) that AntiVirus software flags it as a virus. It makes Apple’s proprietary formats and DRM look pleasant by comparison.

Frustration was setting in — the both consensus iTunes replacement and Internet Freedom Fighter recommended options did not pull their own weight. So I turned to a dear old friend: WinAMP.

And while we were creeping closer to a proper solution, it still lay just beyond our grasp. WinAMP was by far the best music player used thus far — it worked wonderfully. Yet it still did not synchronize song metadata in the manner that I was hoping for.

Could nothing match iTunes? How is it that a piece of software first designed in 2000 is still the best option for synchronizing music more than ten years later? Surely this shouldn’t happen.

If you are looking for somebody to copy Apple, I thought, look to Microsoft. Windows Media Player was dutifully booted up. It was as bad as I remembered it being, and even refused to recognize my phone as a device to which music could be synchronized.

My last, best hope was MediaMonkey. My research told me that it was the refuge of insane music hoarders, the best tool out there for managing a music collection on your PC. And surely the best music manager in the game must include easy synchronization with the most popular mobile Operating System out there.

Right?

Wrong.

MediaMonkey was breathtakingly efficient at adding all my music, pulling in every rating and playcount from iTunes. It had an answer to everything.

Except a friendly solution to Android synchronization.

It’s strange, because I am not even using iTunes to synchronize anything — I use a third-party tool in order to synchronize over my WiFi connection easily and painlessly. If iSyncr can be built for iTunes, surely it can be built for MediaMonkey.

But in our world full of crowdsourcing, filled with super-intelligent app-writing geeks, the application doesn’t seem to exist.

And I’m still stuck here holding one last rotten, stinking Apple.