Cloud and Connectivity
Connectivity is often seen as the albatross around the neck of Chrome OS. Most Chrome apps are online apps running on a remote server, working with data also held remotely. Pull the connection and you can't access either. Reliance on connection is not a problem in an office with a stable Wi-Fi, but it is on the move, or even in areas where connectivity is slow or flakey.
To mitigate this, Google cleverly made its Drive app a core part of Chrome OS, so data can be cached locally and synced in the cloud when connectivity returns. It also made it possible for apps to run offline through Chrome extensions, so that they would keep working even when there was no internet to be found.
Finally, Chrome OS now supports small native apps which run direct from the Chromebook or Chromebox. These are often small and limited in scope or features, but you can use them to make notes, sketch out a document or make quick adjustments to a photo. Sometimes it gets a bit clunky - Google Docs documents created offline sometime fail to sync with Google Drive without some prodding but the offline experience is improving all the time.
Windows doesn't have this problem unless you're using online apps or services. Applications all run locally and of course data can be synced to cloud services if you wish. Microsoft is pushing OneDrive as the default location for saving documents in Office or SharePoint and OneDrive Pro in an enterprise environment but you're free to work in any way you please. As a result, Windows is less reliant on an internet connection.
This comes down to the requirements of your business, and most of all where your users will be working. If the answer is mostly in the office or at home, then Chrome OS is suitable, and there are advantages in convenience and accessibility to having everything stored online. However, for a more mobile workforce where connectivity can't be taken for granted, Windows remains the top dog.
Winner: Windows, Microsoft's approach to the cloud is more flexible and works better on the move, though Google's cloud-first approach has its strengths.
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