Is the issue limited to Apple? What's about other ecosystems and app stores?
If you're in a complex situation where you live in a second country, there's almost always a problem with buying stuff online if you need to bill in one country / ship to the other - and workarounds like needing to create two accounts are pretty common IMO (though usually it's just a case of needing to use a CC from the right country or having the billing address be your address in country A, but having the country field set to country B).
So no, apple's not too unique in this situation, but I've never experienced being unable to access stuff that I bought in one country (though I stay away from buying digital copies of movies etc for this reason), and I've definitely never heard of another company charging for this type of legitimate support, so they're likely unique there.
Go to support.microsoft.com. File a request for any consumer tech support problem. Boom, before you've even spoken to anyone, you've gotta fork over $59. It actually charges your credit card online before you get to speak to someone.
Apple at least always answers your calls and provides advice before attempting an upsell to AppleCare. With Microsoft, you're going to be shelling out a minimum of $59 just to get them to open a chat window. That's assuming you're using a consumer Windows product. Use an enterprise variant or server OS? That'll be a minimum of $295 to talk to a human.
Microsoft don't charge you to talk to a person when you have issues activating windows (and I've never had one of their products break when I changed region). I've never had to deal with any of their services breaking for me (only products) so I'm not sure whether they try to sell you a support subscription when you use eg http://support.xbox.com/en-GB/contact-us?isChatCallAvailable... , but I'd expect it to be free if it fell into the category of "stuff I purchased that you failed to deliver to me".
This isn't unique, new, notable or even newsworthy. It's just how digital goods purchases work. Welcome to 2007, people.
I think there may have been some misunderstanding here regarding his App store account though; I also see a comment on his blog indicating this. I moved from Europe to the US and can't remember having any problems moving my account to the US. I can imagine that it's problematic to have two accounts on the same device though.
I suspect one of the reasons Apple hasn't "fixed" this is because doing so would require renegotiation with content providers, who'd most likely push for even more customer-hostile restrictions.