Office 365 after a year: Worth it or not?

I've been relying on the Office 365 Midsize Business subscription for just over a year now. After a baker's dozen of months, I thought it would be a good time to review the good and bad of this service, especially for those of you considering jumping into the Office 365 ecosystem.

Before I get started, let's set the stage. First, and most important, you should know I pay for my own subscription. I didn't get any "press favors" with this thing. I signed up like a regular business customer and pay for it like a regular business customer. With subscriptions for me and my wife, that comes to $30 a month.

I bought the Office 365 Midsize Business plan, not so much because my professional service firm is a midsize business as because I use computing resources like a midsize business. I've got well over 100TB under one roof, somewhere around fifty devices on our network, and GigE into every wall of the house. So I bought the larger plan because we have a lot of data to store, mostly email going way back to before the turn of the century.

For those of you curious why I chose Office 365 over Google, go ahead and read My big email switch: Why I picked Office 365 over Google Apps. It tells the full story.

For the rest of this article, I'm going to go down the various features and elements of my Office 365 subscription and detail to you my impressions after a year. What I'll measure against is whether or not the $360 we spent for the year was worth it or not.

Finally, let me note that everyone's usage pattern is going to be different. What I value or need may be different from what you value or need. In any case, this is my experience.

Email Exchange service

I've been using hosted Exchange services for well over a decade. Prior to moving to Office 365, I was using a private provider and paid $20/month for two Exchange email boxes.

I made the transition to Office 365 because the small hosting provider was starting to evidence reliability problems and I rely on email for just about everything I do.

After a year: Reliability problems have all but gone away. I have had no performance or functionality problems with the basic service of getting and sending email. Spam management is mediocre (I still get messages using foreign character sets), but the amount of junk I get is moderately manageable with rare false positives.

I judge Office 365's basic Exchange hosting services as a win.

Support quality

When I first tried setting up my accounts with Office 365, I ran into some snags and had pretty high quality support from the Office 365 support team. Since then, service quality has diminished. I dread using Microsoft's support services. It's a painful and often frustrating exercise.

After a year: Support is barely adequate. It's a complete gamble whether I'll get excellent support or terrible support.

I sent in an email request for support on May 6. In response, I got a form letter that indicated the support rep hadn't bothered to read my request. After sending back a scolding response, I finally got a useful answer today -- a full seven days after my request was initiated.

I judge Office 365's support services to be barely tolerable. It's there, but it's not good.

Microsoft desktop applications

One of the benefits of the plan I have is that each user can install up to five copies of the Office desktop applications. Both my wife and I move between three main machines, so we'd wind up needing six licenses to office. In addition, I also use Office on my Mac, which would be a seventh license.

Since we pay $10/month more for Office 365 than we did just for Exchange hosting, our cost for what is effectively seven Office desktop licenses is $120/year, which is a pretty fair deal.

After a year: Microsoft promises free upgrades to new Office versions, but there have been no new Office versions. The PC version is not bad, but could use some improvement. The Mac version of Office feels like a bad piece of shareware. It's painful to use, and hasn't been updated for something like four years.

I judge Office 365 desktop applications to be a reasonable deal, but the lack of upgrades and new features is disappointing. The shareware-quality Office for Macintosh is just plain inexcusable.

Next: Office Web applications and OneDrive...

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Office Web applications

One of Microsoft's selling claims for Office 365 is the availability of Office Web applications, similar to the suite of Web apps that Google offers.

Of the Office Web applications, the only one I have used is OWA (Outlook Web Application). Web implementation of Outlook is terrible. First, for some reason, its interface is entirely different (and less usable) than the interface for Outlook.com, and you can't use Outlook.com with Office 365. Go figure.

Second, as I said, the interface is terrible. You can't even specify the columns you want to see, so the bulk of the screen is filled with a subject line sitting on top of the sender name. No other particularly useful message information is provided without opening the message, and the application wastes tons of screen real estate.

There are arrow icons in messages, but they're for forwarding or replying, not for moving back and forth between messages. It is painful to use.

As for the other Office Web applications, the simple fact is I have yet to even launch them. You can't just login to your Office 365 account and launch an app. You have to go into OneDrive or SharePoint and then create a new application file. Too much work, especially since the Web variants are reportedly much weaker variants than the desktop editions.

After a year: I've been able to derive no value from these at all.

I judge the Office Web applications as a major disappointment. In particular, Outlook.com (which is a completely different app than OWA) showcases just how bad Outlook Web Application is. It's also disappointing that you can't use Outlook.com with Office 365.

Contacts and calendar

I'll be talking more about contacts in a future article. As it turns out, contacts in Office 365 sync nicely with the iPhone, but poorly (they lose categories) with Android devices. Disappointingly, given that Microsoft owns Skype, Skype contacts live in their own silo, and don't sync with Outlook contacts.

The Office calendar has improved over the years, but I use Google Calendar and completely ignore the Outlook calendar. When I made the decision to use the Google Calendar, there were some valuable features (emailed reminders) that didn't exist in Outlook's calendar. Some of those features have since been added.

Even so, my Google Calendar is so solid and useful that I haven't tried to fight to get the Outlook version up and running.

After a year: A solid and reliable Google Calendar has given me no reason to consider switching to Outlook, combined with Outlook's inability to share contacts with Skype.

I judge contacts and calendar as adequate, but not compelling.

OneDrive for Business

In typical Microsoft fashion, the company has OneDrive and OneDrive for Business -- and they're completely different beasts. When I first got my Office 365 account, OneDrive was called SkyDrive and OneDrive for Business was called SkyDrive Pro. Apparently, Microsoft had landed on someone else's trademark and had to change the name.

I don't use either service. I'll tell you why. When I first got Office 2013 with my Office 365 account, I tried to save my files to OneDrive (what was then called SkyDrive). The desktop applications wouldn't let me. That's because the OneDrive it wanted to save to was a consumer version of the service, so even though I had bought the business version of the service, the applications that came with the business version of the service couldn't save to that version of the service.

Still with me?

Microsoft has just announced that it's increasing the allocation of OneDrive for Business to 1TB, which is pretty impressive. Sadly, because OneDrive for Business is based on SharePoint, files uploaded to the service are slightly modified.

As a result, while I'd like to just dump my entire documents folder into a shared OneDrive for Business, I don't dare. I don't want all my carefully crafted code and files to be mucked with just because I might want to store it in Microsoft's cloud.

After a year: Microsoft's cloud offerings are still baffling and annoying. While the 1TB offering is generous indeed, its value is substantially diminished by the problematic rewriting of content stored using the service.

I judge OneDrive for Business a service Microsoft didn't have to screw up. If they just made it basically a Dropbox clone, it would be invaluable. Instead, there are two different versions, with logins that are incompatible, and you can't even save your Office 365 files to the OneDrive for Business you get with Office 365. Short answer: WTF?

Also, while we're on the subject of authentication, if you have an Office 365 account, you can't use that account to sign into Windows 8. Windows 8 requires your Microsoft account, which maps to OneDrive, not OneDrive for Business. It's as if Windows, the Office desktop apps, and OneDrive come from one company and the Office 365 service and One Drive for Business comes from another.

Next: Mobile versions of Office, SharePoint, and overall dollar value...

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Office for iPad, iPhone, and Android

My ZDNet colleague James Kendrick calls Office for iPad one of Microsoft's finest moments.

I use the built-in email application on my Android and iOS devices to access my Office 365 email. Microsoft's OWA app is terrible by comparison, with big rows and minimal useful information inside the glossy interface.

I don't have much use for Office for iPad (even though I can download it for free) because I don't have a good way to link OneDrive or OneDrive for Business into my daily workflow. See my discussion about OneDrive on the previous page.

Finally, my Chromebook beats the pants off of my iPad as a go-out-and-about device. It's both less expensive and runs full Chrome, along with my extensions. I need Chrome far more than I need Office on the iPad.

I'm a very active PowerPoint user, but I don't work on PowerPoint presentations when I'm out because I have a very large media asset library that lives on my LAN and create very big PowerPoint files. So even a moderately good PowerPoint on the iPad doesn't provide me with much value.

After a year: Microsoft has clearly improved its mobile offerings. I just can't find myself caring.

I'll let James Kendrick judge Office for iPad, and he's very happy with it. I still think Office for iPad is crippled -- like the rest of Office -- with the inconsistent account and identity management foisted on users by OneDrive and OneDrive for Business, Microsoft accounts, and Office 365 accounts.

SharePoint and OneNote

I can't tell you how excited I was when I got Office 365 and, by virtue of my subscription, now had a full SharePoint installation.

I don't use it. At all. I haven't been able to convince my colleagues to use it with me.

I also don't use OneNote, even though it's substantially improved over the year. Instead, I use Evernote. Had OneNote been as good as it has gotten before I dumped all my stuff in Evernote, I might have used it. But now that I'm invested in Evernote, it's just too much work to move things to OneNote.

After a year: I haven't been able to convince a single collaborator to use SharePoint. Everyone is fully comfortable with Google Drive, and just about everyone I work with shares documents via Google.

I judge SharePoint disappointing. You need other people to be able to use this product and SharePoint is being left in the dust by other collaboration tools, at least among the people I work with.

Lync

Lync is Google Hangouts and Skype... on steroids. Unfortunately, it has a terrible client for Mac use, and I do all my video conferencing on the Mac.

Update: This critique has been corrected based on feedback from Microsoft. When I originally started using Office 365, Lync and Skype couldn't talk. Since then, that has changed. See my notes below.

Once again, contacts become an issue, because Skype doesn't share contacts with Lync, and you can't use Lync to talk to Skype users. As a result, if you're going to do a Lync conference, everyone has to have Lync, and except for a few Microsoft employees I know, very few people ever use the product.

After a year: Lync's integration hasn't improved. I was just informed by Microsoft that, "Lync and Skype are currently federated for IM, presence and voice calls and have been since May 2013 (this link provides full description). Lync users add Skype contacts by typing their Skype users' Microsoft account names into the Add Skype Contact window in Lync."

I judge this to be another missed opportunity good progress, but it's interesting that as an Office 365 user and a Skype Premium customer, I never got any "in my mailbox" notification of this change. Apparently, it was posted on a blog entry, but outreach to at least this customer didn't make it.

Overall dollar value

After a year, has Office 365 been worth it? Given the fact that I use roughly a third of what my subscription offers, I still consider it worth the money.

Google Apps doesn't offer the depth of Microsoft's desktop applications and given that I'm a very heavy PowerPoint user, I'd still need to buy Office. Also, even though none of the desktop applications have seen an upgrade in far too long, the desktop Outlook experience is still far more convenient for me than Gmail.

So, without a doubt, Office 365 is worth the price. The big disappointment is that it could be so much better... if only it didn't suffer from Microsoft's usual baffling product management decision making.

Now that OneDrive for Business offers a terabyte of storage, I will do a test install of OneDrive for Business and run some tests to see if it damages any of my important files. If the service doesn't completely suck, it's just too good a deal to dismiss without at least some investigation.

Would I advise you to invest in Office 365? Well, that depends on which ecosystem you rely on. If you've got a long history of relying on Microsoft, then Office 365 is a good deal, if a bit frustrating. But then, if you've got a long history of relying on Microsoft, you're used to getting reasonably good software served with the occasional heaping helping of annoyance.

Bottom line, though, if you add up the suite of desktop apps, the Exchange and SharePoint services (whether used or not), the 1TB of online storage, and all the fixin's, Microsoft is certainly providing value. I'll keep using the service for another year.

What about you? Have you been using Office 365? Has it proven to be valuable to you?

By the way, I'm doing more updates on Twitter and Facebook than ever before. Be sure to follow me on Twitter at @DavidGewirtz and on Facebook at Facebook.com/DavidGewirtz.