Note: This post is part of a series on my move from Gmail to Office 365. To see a complete list of related posts, see Summary: Moving to Office 365.

In my previous post, Reasons for Moving from Gmail/POP to Office 365, I described many of the limitations of my Outlook/POP/Gmail approach to managing e-mail. In this post, I’ll talk about the reasons I decided to take the plunge and move to the Office 365 Preview.

Based on the issues I had with my older configuration, I decided to look into Outlook.com and Office 365 as a solution. Here’s a list of the primary benefits. For the most part, these improvements directly address the problems listed earlier.

Note: Some of the following also applies to Microsoft’s free e-mail offering, Outlook.com, but this section focuses on Microsoft’s hosted Exchange / Office 365 service offering.

Office 365 Messaging Benefits

• Improved Web/Client Interface: Though I occasionally used the Gmail web-based interface, I could never stand to use it for more than just the most basic messaging tasks. The process of organizing, replying to, and sending messages was too cumbersome for me. I tend to format my messages with tables and other options where needed, and that was just too clumsy for me to perform via the web interface. I know that a lot of people like Google’s approach to a conversation-based views and the use of labels instead of folders, but I found the process of organizing e-mail to be so tedious that I wouldn’t do it. Instead, I always used the full Microsoft Outlook client wherever possible. Though that required other services to back up the local .PST file, I was able to use a much better user interface. The updates to Outlook.com and Office 365 changes all that for me – I can now use drag-and-drop and familiar keyboard shortcuts to create and manage messages. It also manages my Contacts and Calendar without the use of other integration methods. And, with the ability to perform on-demand installations of Outlook directly from the Office 365 Admin page, I can make sure that I get the full Outlook client installed and configured on my frequently-used Windows machines.
• Elimination of PST File Synchronization: With Office 365, all of my data is stored online and there’s no need to synchronize and backup separate .PST files. I can now keep Outlook 2013 open all day, every day, on several different computers and mobile devices and I never have to worry about missing any changes.
• Efficient Local Storage: While cloud-based access has been reliable for me in the past, for performance, backup, and peace of mind, I prefer to have a local cache of my data. Outlook 2013 uses a more efficient, compressed .OST file format that keeps all e-mail synchronized locally on my machine. Outlook 2013 provides some great improvement for Cached Exchange Mode though .OST file improvements. You can now specify how much data is cached locally, and the .OST file sizes benefit from compression (in my tests, I got around a 50% reduction in storage space when I compared similar .OST and .PST files). For more information, see What’s New in Outlook 2013.
• Consolidation / Historical Data: With Office 365’s generous storage space (25GB per user, in my plan), I was able to transfer all of my historical e-mail to a single hosted Exchange account. I no longer have a need to archive data in separate PST files or periodically strip out attachments. By default, Outlook will cache one year of data locally. That’s probably plenty for most users. On my primary computer, I chose to download the entire list of messages for easy indexed searching.
• Better support for mobile devices: While IMAP (and, to a lesser extent, POP) are acceptable options for accessing e-mail on multiple devices, it can be a tedious and error-prone chore to keep track of folder structure, calendar items, contacts, and changes from multiple devices (especially those that are occasionally disconnected from the server). With Gmail, I relied on the Gmail Notifier and Google Calendar Sync applications (both of which are years-old and poorly supported) to try to keep things in sync. With Exchange Active Sync, all of this works flawlessly (so far) on my Android Phone (Motorola Droid), Android Tablet (ASUS Transformer TF101) and Windows-based machines.
• Attachment Archival: With the storage space offered by Office 365, I no longer need to worry about archiving off attachments to keep my .PST file small enough for frequent backups. No need to remove attachments due to unlimited storage space.
• “Automatic” backups: An obvious benefit of having all of my messages stored online is that there’s less of a need for local backups. I still periodically export my data store to a .PST file, but that’s a quick and simple operation.
• On-demand / Streaming installations: The ability to automatically download, install, and configure an instance of Office 2013 in a matter of a couple of clicks is really powerful. Occasionally, I’ll be working in a VM or on-site on a client’s computer, and the ability to use a full-fledged e-mail client is excellent.
• Spam / Junk-Mail Filtering: Over the years, I have received as many as 24,000 spam messages per month. Thanks to Gmail’s excellent spam filtering, only an extremely small number of bad messages would get through. So far, Office 365’s spam filtering has seemed to work fairly well, though I’ll need more time to evaluate how it compares. I do like the ability to quickly and easily allow or block specific senders, though.
• Push-Based Notifications: In my POP-based approach for receiving messages, I had configured Outlook to regularly poll for messages. It worked fine, but there was a potential delay of a few minutes before I received messages. Unfortunately, that little delay is often enough for some of clients to start to panic when they don’t get a (really) quick response to an issue. With Exchange-based messaging, I can get near-instant notifications to my desktop, laptop, tablet, and mobile devices.

Sounds good. How do I sign up?

That concludes the “short list” of potential benefits of my e-mail migration hopes and wishes. In the next post, I’ll provide details on how I migrated to the Office 365 Preview.