Five years ago, just before Microsoft Vista was released, our household CIO made a strategic decision. We would move to OS X.
It wasn't a hard decision. The cost of supporting both XP and OS X was too high, XP's security, debugging and maintenance issues were intractable, and OS X had a much more interesting software marketplace. Moving to OS X would dramatically reduce our cost of ownership, which was primarily the CIO's opportunity cost. Time spent managing XP meant less time spent on my health and on family joys and obligations. 
Except I am going somewhere. I will fade. So will you, though there's a bit more hope for the under-30 crowd. We might be able to slow the natural deterioration of the human brain (aka "Alzheimer's" and its relatives ) by 2030. It's too late for the boomers though, and probably too late for Gen X.
Sure, I'm still the silverback of the geek tribe. I may have lost a step, but between experience and Google I still crush the tough ones with a single blow.
Not for long though. I give myself ten years at most. I won't be able to manage something like OS X version 20, and I don't want to be reliant on my geek inheritor - son #2.
We will need to simplify. In particular, we'll need to simplify our tech infrastructure (and our finances  and online identities  too).
So our next migration will be to iOS - a closed, curated, hard target, simpler world.
You'll be going there too -- even if you're not fading (yet). The weight of the Boomers  will shift the market to Apple's iOS and its emerging equivalents. Equivalents like ChromeOS, now turning into iOS for desktop device with its own App Store .
I still have a few years of OS X left, including, if all goes well, the 11" MacBook Air I've been studying. The household CIO's job, however, is to think strategically. Our future household acquisitions will shift more and more to iOS devices, possibly starting with iPad 2.0 (2011) .
I expect by 2018 we'll be living in largely iOS-equivalent world, and so will you.
 I miss Quicken 1996 -- before Intuit went to the DarkSeid.
 The 2016 remake of Logan's Run will be a smash hit.
 I bought iPad 1.0 for my 80yo mother -- same reasons.
 1989 was when the National Institutes of Health needed to launch a "Manhattan Project" style dementia-management program. I wasn't the only person to say this at the time.
 If their first netbook device doesn't come in under $150 with batteries Google is in deep trouble. Android is not an iOS-equivalent, it's a lot more like XP.
 Pogue's 10 year tech retrospective is a beautiful summary of the costs of making the wrong household tech decisions. He misses the key point though. The real costs are not the purchase costs, or the immense amount of failed invention, or the landfill costs -- it's the opportunity costs of all the time lost to tech churn. I've a hunch this opportunity cost is important to understanding what happened to the world economy between 1994 and 2010. That's another post though!
 Digital identities proliferate like weeds. Do you know where all your identities are?