Applications
This is where Windows pulls ahead. While the Windows store isn't packed with awesome business applications, it doesn't matter. Windows has Microsoft Office, the gold standard in office suites, and you'll find software from all major vendors available, excluding Apple. Whether you need accounting, backup, photo-editing and video-editing, project-management, technical drawing or engineering applications, you're guaranteed to find the big-hitters on Windows.
This isn't a knockout blow, however. Not everyone needs big, flashy applications to be productive. In reality, many users only use a fraction of the features in mainstream apps, like Word or Excel. There's no reason why employees couldn't use Google's office apps or the other business apps available through anything with a Chrome browser. They're lean, efficient, easy-to-use and perfect for collaboration.
What's more, many big business applications are moving to a cloud-based, SaaS model, anyway. Saleforce.com, for example, will run on a Chromebook, while there is a huge range of CRM, collaboration, accounting, logistics, marketing and invoicing services, all of which will work on Google's OS. A lot of the good stuff is free, or relatively inexpensive for a smaller business so there are savings to be made.
In fact, the biggest problem isn't so much finding applications for your needs as choosing between them. With a lot of smaller developers on the market and too few sources of credible reviews, it's a challenge to zero in on the best apps.
Windows 8 was meant to jumpstart a wave of smart, focused, lightweight business apps, but so far this has yet to materialise. It might simply be the case that these apps have already found their home in the cloud, where Chrome OS is ideally placed to take advantage of them. And while Microsoft doesn't like to draw attention to the fact, its Office web apps will also work on a Chromebook or Chromebox. If you have users who don't need full functionality, the cheap Office 365 Small Business plan, with email, Lync online conferencing and Office Online might be all they need.
Winner: Windows 8.1, but if your company is prepared to try Web-based services or you have employees who can work with Google's Office apps or Office Online, then a Chromebook could easily cover your requirements.
