If you're still using Office 2008 (released in January 2008), then the subscription probably doesn't make economic sense: you run through two or more product cycles between upgrades, so your up front cost is amortized over six or more years. Even with four computers, you'd be only paying $560 after six years' of use, versus $600 for six years of Office 365.
But if you do keep your Office licenses current, the subscription looks more inviting with three or more computers. Consider a family with three Macs, all of which have had Office 2008 and Office 2011 installed. Assuming the same $140 price for Office 2008 as Office 2011, the total cost would have been $840 (half for Office 2008, half for Office 2011) over the last six years.
If the Office 365 subscription option had been available at Office 2008's launch, the total cost for those same six years would have been $600, or a savings of $240. In addition to saving money, you would've been able to install Office on two additional computers, and up to five tablet devices, for no additional money. You'd also get 60 minutes of free Skype calls each month, and 20GB of SkyDrive cloud storage for each of up to five users.
So now, the decision isn't quite so easy, is it? The subscription offers more features, covers more devices and users, and costs substantially less. Subscribing seems like the obvious choice with three or more computers and regular Office upgrades, right?
It does, but there's one more key question you need to answer first: Do you intend to keep subscribing? If you do, then yes, subscribe.
But if you're not sure if you'll keep subscribing, then it's a tougher decision still. Because, like leasing a car, when you subscribe to your software, you don't own anything at the end of the subscription term. Let the subscription lapse, and you'll find yourself unable to edit your Office documents. So if you stop subscribing, at that point you'll need to purchase "real" copies of the software, which will obviously increase your costs.
If you are going to stop subscribing at some point, it's best to do it when a major release has just come out—that way, when you purchase the "real" apps, you can expect to get three or more years' use out of them before the next major release.
Whew. That's a lot of work to decide if an Office 365 subscription is right for you. Boiling it down to its simplest essence:
- Subscribe if you need Office on your iOS devices, as it's the only way to get it.
- Do not subscribe if you have no need for Office on iOS, and have only one Mac.
- Possibly subscribe if you have two or more Macs, depending on how often you upgrade Office and your likelihood of continuing to subscribe.
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