Here in Canada, the iPhone is available on all carriers and you rarely see an Android phone. The iPhone totally dominates the market. Most smart phones are iPhones and Blackberrys.
It's almost like the carriers here are trying to hide the Android phones. Anyway, I am certain that low Android adoption in Canada has more to do with it being difficult to get than about consumer desire.
If a developer and nerd who knows about Android (me, for example) has a hard time buying one, think about the average consumer. There's no way an average Joe would buy an Android phone in Canada over an iPhone.
And they refused to sell it to me.
The girl at the counter said that because it's such a popular phone they only sell it with 3 year contracts.
I bought the at&t version on ebay a few hours ago but still, it's ridiculously hard to get an Android phone whereas iPhones are everywhere and pushed hard.
So what you're saying is further multiplied by all the businesses who chose Win 95 over Mac OS 8, then stuck with Windows when upgrading their equipment.
On top of that add that Microsoft was making a lot of money from their OS and Google doesn't...
I don't see why you need to see the world in terms of easy patterns. I'd say that enough variables have changed since then that any prediction based on analogies is very uncertain.
Second is that the iPhone still has a slim apps edge (though its narrowing quickly, Android is very close to parity. One thing that kept many folks on MS products were the apps built for that specific to Windows (Office primarily). I don't think you're going to see the same phenomenon in the mobile app space.
So assuming you see the iphone on another carrier (and soon) I think you'll see the marketplace pretty evenly (50% +- 10) split between iPhone and Android for some time.
1) Apple had a large advantage over Microsoft too... they just wasted it. Those were the dark days of Apple: MacOS 7 was alright but less than brilliant and then they got stuck with the Copland project (the Mac version of project Longhorn). In the meantime Microsoft got Windows 95 out, and had several years to solidify its position.
2) Apple sold expensive computers back in the days. I don't mean the high end like today but actually expensive. The idea was that if there's so much demand we may as well milk the cow for all it's got. If I remember correctly Steve Jobs believed in lowering the price and going for marketshare, whereas Sculley thought better to get as much money as they could out of it. Eventually the latter one. This was another reason that made Apple lose marketshare
3) The customers for iPhones, Android phones or other smartphones are in reality the carriers. And they are very worried of losing their bargaining advantage (plenty of supply from different companies, but only few carriers to buy them). Hence I expect they'll try to avoid having anyone get a large marketshare. They may back Apple, Google, Microsoft, RIM and Nokia as it is to their advantage.
Finally a last difference is that Microsoft made a ton of money from their Windows product. Google is making little money from their Android. I am not sure what the implications of this will be, but it may matter a lot.