I got my first iPod before there was even an iTunes app for Windows. I purchased a Firewire 400 PCMCIA card for my Dell laptop to make syncing easier with Musicmatch.¹ The reason I purchased an iPod, over other MP3 players at the time, was how well Apple had thought out how to integrate the MP3 player to the user experience. You could just effortlessly listen to anything stored on your iPod. There was almost a little bit of magic in how Apple had fused the device to the experience.

For a long time I had invested in the Microsoft ecosystem. All my computers and devices spoke to each other the way Microsoft wanted them to speak. Over time Microsoft showed they weren't capable of handling a digital ecosystem - dropping PlaysForSure for Zune and then dropping Zune for Xbox Music. I loved my iPod and eventually looked at what else Apple had to offer. I made the switch to my first Macbook Pro laptop, and as time has gone on, I've continued to purchase more products from Apple. My purchasing choices weren't based on the idea that Apple's hardware was so much better than everyone else's. It was that purchasing Apple devices, and using them together, made them worth more than the sum of their parts. The ecosystem, not the hardware, is what I was buying into.

My worry is the ecosystem I've invested in is no longer working as promised.

This fall Apple released iOS 8 and Yosemite with the promise that using these two operating systems together would blur the lines of how you used Mac and iOS device. One of the common questions I've been getting this holiday season is on media collections - managing pictures, music, movies, etc. - with everyone's brand new Apple device. I have family and friends who have purchased iOS devices, or switched to OS X, because of my previous recommendations or on what Apple promised to all of us in 2014. Unfortunately as I look toward 2015, it feels like Apple hasn't kept their promise. Using my Mac and iPhone together is no longer a "more than the sum of their parts" kind of experience.

So as family and friends have asked how to do more with their devices, I've been less and less inclined to automatically tell them about another Apple device to expand their media experiences. Apple has kept a frantic pace of adding new features and functions. This pace has caused some serious setbacks on long standing features and made what was previously an easy recommendation something I've had to pause and reflect on.

The first issue I've had with Apple this year is the one step forward, two steps back approach to basic features. Three things that stood out to me with iOS 8 and Yosemite:

• Music Playlist Editing: It's almost 2015 and we've had playlist folders in iTunes for over 10 years. In 2011, Apple introduced iTunes Match. This allowed an iOS device to create and manage playlists on your device. These steps forward are moot with iOS 8 because users cannot edit playlists inside a folder.
• Audiobook Chapters: Audiobooks have been apart of iTunes since v3. Overtime the emphasis of audiobooks has ebbed and flowed, but being able to play an audiobook on your iOS device has been a standard feature. With recent releases, a simple feature like chapter selection has gone missing.
• iTunes UI: iTunes UI and play features are a step back from previous generations of OS X. Simple things like shuffle and repeat buttons are missing and have to be controlled via the menu instead of on the music player UI.

My worries aren't with just the iOS 8 and OS X Yosemite, but everything Apple has taken on to support their updated ecosystem.

• App Store: When App Store opened in 2008, it ushered in everything I had hoped my iPhone would grow into. Now in 2014, the App Store is the running punchline of a series of bad jokes. App developers are told to roll back features after Apple themselves promoted said app in the App Store. Only to have the choice reversed after public outcry on cloudy guidelines. Counterfeit apps continue to get through Apple's review process. All of this caused some OS X developers to abandon the App Store and release updates or new versions of their software independently
• Secondary Features: iOS 8 and Yosemite promised so much, but fell so short. Family Sharing, iCloud Drive, Continuity, Handoff, and iCloud Photo. These all sounded amazing from the 2014 WWDC presentations and the bilingual live stream of the iPhone 6/6 plus release. The problem is none of these features are working as Apple has promised.
• Media Management: Beyond the iTunes UI problems I mentioned above, iTunes 12 overall is a navigational disaster. I can understand the need to update and move forward with iTunes, but the change to navigation and functionality makes the transition from iTunes 11 to iTunes 12 feel more like the transition from Windows 7 to Windows 8. The experience feels forced by the software maker and with zero input from the user community.

When you look at how Apple releases their hardware, maybe it's time they do the same on their software side. On the hardware side, Apple releases a new device one year and then tweaks the same design with small upgrades and corrections the following year. Now imagine the stability and speed of iOS and OS X if one year is about the new features and functions and the following year is spent to make these features work faster and smoother. Apple did this once with Snow Leopard and it was met with dull clapping from the media, but overwhelming praise from the user community.

Here's hoping 2015 turns out to be the year of the Snow Leopard's return.