I'm not surprised he has those complicated charts in his article. I've dealt with this issue myself. The quick summary is that all this would go away if there wasn't customer-hostile DRM and sandboxing in the entire ecosystem the purpose of which is to control and regulate my access to things I own. This is never a benefit and always a burden. As it is, I often find it a nightmare to get my content where I want it and have vowed to use Android only in the future. i-* was a mistake for me to get involved with.
Actually, only two of those tens of services have anything to do with DRM: apps and iTunes.
For apps: if you stick to free apps, like most Android users do, the point is moot. If your family has more than ten devices, buying a second copy of that $5 app is honestly not a huge burden. If your spouse buys their own apps like any other adult, you can support up to 18 iPhone-toting offspring total, which seems reasonable.
For iTunes: I thought it had DRM-free music now? In which case, you can copy that music on all 200 of your extended family's iPods. What you can't do is let 200 people buy music in your name, but I don't see why you'd want to.
Everything else is unrelated to DRM. It is a mess, yes, but not for DRM reasons.
On the iOS App Stores, everything is region-locked and DRM'd, even those which are free. Sticking to free apps isn't an opt-out of iOS's DRM.
For example, even though Apple advertises "the App Store", there isn't an App Store. There's one per country. I've seen some cool apps mentioned on blogs and such that I would love to have, but even if they are free, if I'm not in the right country, I can't download them.
(Yes, I could probably 'jailbreak' my iPod, or sign up for an Apple ID with a fake address, or some other nonsense. Doesn't change the fact that Apple's DRM has such restrictions.)
It seems funny to me that Amazon has no trouble shipping pretty much any item from any country to any other country, but Apple can't deliver bits across borders.
I don't disagree with your comment, but Amazon do have trouble shipping items across countries, if I go to Amazon.com right now, 8/15 of their "recommended" items for me are being marked as "We are not able to ship this item to your default shipping address." This selection is even narrower with a country-specific Amazon, e.g. Amazon Japan only ships books and movie DVDs internationally but nothing else.
That phrase was not meant to be condescending. What I mean is that, while I can see why you'd want to share apps with your children, your adult spouse is their own person and can buy their own stuff. The article claims a 10-device limit may be too low for families, and I'm pointing out that two people remain two people even if they marry.
