As obsessive as it may sound, I currently own – and regularly listen to – a collection of more than 76,000 songs via my iTunes account. The display of accumulated hours at the bottom of my iTunes homepage tells me that if I were to hit “Play” at the first song (by a punk band called “A”) and let it run continuously, it would take a little over 386 days to reach the last song in my library (by a string quartet called “999”).

I store the bulk of this music, spoken word, and movies on a 2 Terabyte external hard drive, which I always keep plugged via USB into my Macbook Pro and may stream through my Apple TV continuously, as needed.

I should mention that I manually uploaded at least 95% of this collection to my store-bought external drive (which, when plugged into my Mac, combines with and is shown and is accessible in my iTunes library) via my personal collection of CD and DVDs, which is why I found Apple’s iCloud especially appealing. You see, one of the perks is it allows you to transfer as many as 26,000 of your “non-iTunes purchases” (aka CD/DVD uploads from your personal collection) into iCloud, where it is converted to a more pristine, 256-Kbps AAC DRM-free quality file with iTunes Match, for a small annual fee.

iCloud also allows you to share music on multiple devices

iCloud also allows you to purchase music on one device while sharing it with all the devices that are currently in sync with that device. This means that all of the song tracks in my library (as well as any purchased apps and e-books) appear in all connected devices, without the need for manual synchronizing.

The iTunes Match feature allows you to copy ripped music files by matching them against pre-purchased iTunes tracks to help avoid redundant copies of music tracks cluttering up the cloud, and my personal library. Sounds pretty cool, doesn’t it? Well, it is.

But there are a few understandable “flaws” in this system.

For example, the iCloud database does not actually support a browser, making it technically impossible to play the ripped tracks I’m storing in iCloud on devices not synched with my iTunes database.

So, the big question: Is all of this data actually safe in iCloud?

Well, in one respect, the iCloud backup feature can be seen as a “data safety tool” in that it automatically “backs up” all of your data (songs, books, photos, docs, etc) to all pre-synced devices simultaneously, thus creating the feeling of safety in knowing your data is instantly being stored on all of your devices, as long as a Wi-Fi access is available at the time of auto-sync.

In early 2011, there were reports of cyber-criminals utilizing potential security holes in iTunes, and more recently, the Apple’s iOS 5 update.

One reputable blog provided a detailed video on this security snag and wrote: “When a user tries to restore a backup from iCloud, the device automatically fills out the Apple ID field with random email address. If you tap the “Cancel” button, it again pops up with another email address. This issue can lead to a serious problem in future. The bad-boys and intruders may collect the emails this way and can cause some type of damage either to the company or to the user.”

Apple products won’t be free from threats

The good news is that I’ve been running these programs for years now and have yet to experience any of the leaks mentioned above. But, the evidence is clear that as the popularity of Mac products and the number of its users continues to grow, Apple products won’t be as free from threat as was once touted. Reports of infection and threat by Apple users are on the rise and it’s certainly a good idea to keep your personal data protected – especially your music and photos!

Face it, we live in an exciting era where we are witnessing the blurring of lines between our technical work lives and our private lives. Not unlike the Wild West, we find that with each wondrous advancement our technical wizards pioneer, we should expect a period of trial and error – along with the threats that pour in to take advantage of those periods.

Until we live in a perfect world and iCloud is absolutely secure, I strongly suggest you take the extra precaution of utilizing Trend Micro SafeSync – or if you’re partial to Apple products, Trend Micro Smart Surfing for Mac as excellent ways to keep your personal treasures – in and out of the iCloud – safe and secure.

For one thing, SafeSync backs up all files and allows you to share easily, while “bank-level encryption” keeps it all locked up tight – but I also find Trend Micro’s 20+ years in the security game far more reassuring than iCloud’s still-questionable ability to protect music and other digital data.

Hey, it’s your music. Protect it. Happy listening!

PS: For more info about iCloud and what it can do, check out this short video.