I remember reacting with skepticism when I heard that Microsoft was rolling out their famous Microsoft Office suite as a monthly subscription for $9.99 a month. Why pay an endless subscription when you could get the same product for a one-time fee? I viewed it as just another attempt for Microsoft to line its pockets.

So I must say that I am a little surprised to now find myself a subscriber. There is more to the service than I originally thought.

When you have just shelled out $1000 or more for a new computer, there is something pretty painful about spending another $200 or more for Microsoft Office. Everyone uses the software, and having to pay such a hefty fee feels akin to taxes or those hefty extra fees that the airport and city tack on when you rent a car.

I could see how a fee of just $9.99 upfront might ease the sting, and my assumption was that Microsoft figured that they could win customers over with a low up-front fee while secretly turning on a lifetime source of revenue. And this is probably true, but I’ve learned that Microsoft has sweetened the deal in ways that make it much more compelling.

Office 365 comes more compelling if you are installing it on multiple computers

The benefit of the Office 365 Home Premium service is that it includes the full suite (including Outlook and Access), and it covers FIVE computers, not just one. So if you are using this for your family, you can get a lot more mileage for your dollar.

Over the holidays, I decided to finally upgrade my home Mac Book Pro. I had completely maxed out the 256 GB hard drive on my old laptop with photos and video, and the computer had slowed down to molasses with drive filled with family photos/videos and three OS upgrades. I sprang for one of the new 13″ Retina models with twice as much storage on a super-fast solid state drive. I’m secretly hoping that the high speed drive will mean the computer won’t slow down as much even as the drive fills up (check in again three years to find out).

Purchasing a new computer meant it was time to pay the Microsoft Office tax. Somehow, up until this year I have managed to never need to purchase a full-priced Microsoft office license directly. I’ve always had access to an installation option through my work in one way or another. But no longer.

Now, having a new Mac does mean that I have a free alternative to Office: Mac’s productivity suite of Pages, Numbers, and KeyNote. I’m sure that there are some people who will argue very passionately that these products are just as good or better than Microsoft’s. I have looked briefly at Numbers, but my sense is that these are the same people who will tell you that Dvorak is a much more sensible keyboard layout – it may be true, but Office is the product that I know. The secret of using Excel is all the tricks and techniques, and I’m not interested in learning them all over again for a different tool.

To buy the office suite, I could pay $140 for the Home & Student edition, or $220 for Home & Business. I didn’t really need Outlook, so $140 for Home & Student would be fine. Why bother with an Office 365 subscription at $10 a month? I would have the computer for much longer than the 14 months it would take to recoup the costs.

The key came to the fact that I wasn’t planning on throwing the old Mac laptop away. My wife’s Windows laptop was pushing four years old and was also running slow as molasses. I have been trying to convince her to switch to a Mac, and I suspected that if I actually completely wiped my old Mac and installed the OS fresh, it would speed up significantly. However, wiping it meant I would need a new Office installation, and I no longer had access to an installation through work.

My wife was open to trying out the Mac, but I knew that if I gave it to her with anything other than the Microsoft Word and Excel programs she was familiar with, I was going to get the “What the hell is this?” look.

So now I was about to pay a double tax. At $280 for two computers, the Office 365 subscription plan starts to look more compelling. It would now take two years to recoup the savings if I went with the monthly subscription, and that timeline would be closer to three years if I went with the annual subscription pricing ($100 for one year).

And purchasing an MS Office subscription has other benefits. One of the biggest is that it also comes with Access for PC installations. Now, I am the first to admit that Access is a truly awful program. However, one of the Jewish institutions I do volunteer work for uses it to manage its donor database, and a few times a year I need to be able to open it up and edit it. Office 365 would allow me to install Access for no extra cost onto Parallels (this would count as a third of my five computers) rather than paying the $110 for it individually.

There are other benefits, too.  It has 20GB of free storage on SkyDrive, which could be quite useful if I need to send someone some very large files that would overfill my Dropbox account. It also includes 60 Skype world minutes, although personally that doesn’t hold much value for me.

And, each time Microsoft rolls out an update, you get upgraded automatically.

The best part of it is frankly that the software becomes managed on the web. Microsoft’s product keys always annoy me. You have to keep track of them if you ever want to move the installation to another computer. With Office 365, you can manage the installations centrally on the web, deactivating one computer and then installing it on another one.

So, I payed $100 up front for a yearly subscription and installed Office onto two computers.  Three years is a long enough break-even timeline that I am willing to take the plunge.