Why?

• First and foremost: OS X and it's related and supported applications are proprietary. As a result users cannot contribute solutions to problems they encounter. More importantly, Apple simply doesn't have well organized and publicly available infrastructure for feature requests and bug reporting (yes, I know about developer.apple.com).
• I frequently use Apple's forums and never get responses from their staff, which makes me feel like my concerns as a paying customer aren't considered alongside their agenda. I have many posts on there that remain unresolved (for years).
• Their web based platforms are simply insufficient. Google's apps for mail, contacts, calendar, web browsing and more are built off of open source technology and are free to the public - therefore it's widely used and compatible with non-Google products. Apple, however, has demonstrated their incompetence in the area of web based technology with examples like .Mac then MobileMe and now iCloud. Which is still proprietary, costly severely inefficient for a variety of reasons especially if you have business needs.
• More recently though, there were a few issues that I've experienced that really interfere with my tasks at hand.
  • Tunes consistently messes up my iPhone by adding, deleting or changing my apps, files (especially music), etc...
  • My Apple Time Machine recently said it had to update and while doing so it would delete all of my former backups! Obviously this is frustrating because that's the reason I bought it!
  • Messages history doesn't synchronize with Google's Talk. So if I start a conversation on Google, and then switch to Messages, the conversation isn't listed there.
  • Messages on the iPhone doesn't allow you to add multiple accounts (as far as I know) like the desktop version does.
  • Apple Mail doesn't remove drafts after they've been sent.
  • When uploading pictures to a website and selecting them from the iPhoto panel in the Finder, it doesn't reload it on the iPhoto's tab.
  • Can't video/audio/screenshare on Messages over Google anymore.

Obstacles

Benefits

• Improved support. Because Ubuntu is an open source project it is a fact that they are wholly dependent upon their users contributing their support in the form of feedback, patches, testing and more. This persuades me that my voice will be heard and my feature requests or patches will be accepted, at worst by a popular vote. Additionally, since Ubuntu publishes their release cycle I know exactly when a new version will become available, and when support for the current version will end. This helps me, as a business person, prepare for upgrading our digital environment to ensure a smoother transition to the "latest and greatest".
• Improved performance. Ubuntu is drastically smaller in file size than Windows and OS X and, after testing it myself already, I'm convinced I will see a noticeable performance boost. Though I really don't experience performance problems now, except on rare occasion and it's usually related to a poorly written application.
• Improved user interface. Surprisingly, their minimalistic themes provide even more "real estate" on my screen that OS X has. I really appreciate how they utilize the tool bar as a sort of "quick launch" version of traditional applications. This is especially handy for simple tasks like playing media, communications over email and phone based messaging, etc...
• Improved organization. Thanks to the Software Center I have a simple and consistent way of acquiring, updating and deleting applications. Apple required me to drag and drop some applications, while others I had to run an installer. And when I remove an application I'm confident the Software Center removes literally everything related to the application so I don't have fragmented files laying around my computer creating anarchy!

Preparing for the Transition

• Communications over email, telephone and text messaging (both instant and telephone).
• Virtualization for gaming and browser testing websites.
• Entertainment by utilizing services like Google Play and Hulu for videos and music.
• Programming websites which requires LAMP, Git, a text editor and a SFTP client with optional GUI for Git. Android and iOS simulators might be missing though!