iTunes is a Mostly Frustrating Experience and Not Simple for PC Users

Yesterday, I was adding some albums to my iTunes account when I discovered I had purchased the same songs numerous times in the last ten years and they still were not in my iTunes app. I’ve keep an email folder named iTunes receipts and started going through them and they dated back to 2006 when I downloaded the app.

Since iTunes is Apple based and I have a PC (not a Mac)…I’ve always had quite a few issues with iTunes (or at least this is what I thought was going on). If I add a CD to iTunes, it’ll stay in there for exactly two years and then I need to add it again. When I receive a pop-up stating there’s a new update for iTunes and I spend the time to update it…almost immediately afterwards I get another pop up telling me there’s a new update for iTunes available. As you can see, iTunes is a mostly frustrating experience for me. I suspect if I pay the annual fee to put all of my music in the cloud then I may not have these issues, but essentially I’ll be paying for my own music again.

I’ve had my current laptop for at least 5-6 years. Normally, songs stay with the device and even though I backed up iTunes and transferred the songs during the last transition…it seems I lost a lot of the purchased songs from device to device.

I am trying to come up with some ideas that will simplify my music for me. I can switch to Amazons music service (which may be free for me because I have Amazon prime), but then I may not be able use my iPods and music devices I already own.

I could spent considerable time cleaning up my iTunes account and getting rid of the half shell (as I call it) of the songs from my CDs that have been deleted because it’s over the two year limit. And then put together an Excel spreadsheet of all purchased iTunes songs in the last ten years and making sure they are on my device and seeing if iTunes refunds the multiple purchases (which I seriously doubt).

For something that is touted as being so simple, it really isn’t. I listen to music in my car on an iPod, at work on another iPod, when I walk or work out on a small iPod device, and at home through an iPod in a docking station that has speakers. I don’t use the same device for each of these activities.

The choices are almost overwhelming. I might need to spend time cleaning up my iTunes account and then see if I can meet with a specialist at the Apple Store to figure out my best option.

I can’t wait for Web 2.0 when all the apps and devices will figure it all out for me. But of course, that might be a problem in itself.