"History teaches us nothing except that something will happen" - Hugh Trevor-Roper
In the 1990s, the PC market was mostly a corporate market (roughly 75% of volume). Corporate buyers wanted a commodity. They were buying 500 or 5000 boxes, they wanted them all the same and they wanted to be able to order 500 or 5000 more roughly the same next year. They wanted to compare 4 vendors on price with the same spec sheet. They didn't care what they looked like (and they were going under a desk anyway) and they didn't care how easy it was for non-technical people to set them up because the users would never touch the configuration. Nor did they care much about the user interface, because most of the users were only going to be running 1 or 2 apps anyway.
Meanwhile with no internet, home buyers were mainly interested in a PC that ran the same software they used at work (and all of the games were for PC). They may have known Macs were supposed to be easier, but Apple had no shops of its own and what TV advertising it could afford didn't show off the user interface (it's hard to demo an desktop computer's user interface on TV). And, of course, Apple's computers were ultimately beige boxes and not really that much prettier than PCs anyway. And they were significantly more expensive.
Hence, in this market all of Microsoft's advantages were in play, and none of Apple's. Apple, in Steve Blank's phrase, did not have product/market fit. The Open model deployed by Microsoft and Intel produced a generic commodity product that was exactly what the market wanted: Apple's model did not. Fundamentally, Apple's selling points were irrelevant, invisible or both.
Today, of course, Android, combined with chip makers such as Qualcomm and MediaTek, is producing a quite similar flood of generic commodity smartphones. Hence, there's a pretty common narrative that 'we've seen this before' - that the same open approach, producing the same flood of generic commodity product, will crush Apple in the same way.
It would also, necessarily, crush anyone trying to make a living selling high-end Android phones, which are ipso facto much less differentiated from a $200 Android phone than is an iPhone. This is one reason why BIll Gurley suggested Android may be 'the greatest legal destruction of wealth in history' (link), at least for the tech industry.
However, I'm not sure that's true. If one looks again at all of those 1990s PC market dynamics, almost none of them apply to the smartphone market. Phones are NOT generic, fungible commodities:
In other words, Apple has product/market fit in the phone market in a way that it never had in the personal computer market. ALL of the key dynamics that doomed it in the computer market are fundamentally different in the phone market - this time, they all work in Apple's favour, and in favour of the high-end market in general.
Now, it is unclear just how many more people can afford to pay the price Apple charges for the iPhone, and it is unclear how or whether Apple would offer a cheaper product. But the underlying structure of the market is vastly more favourable to Apple than the PC market ever was. Simply chanting 'open wins!', as though you suffer a form of tech Tourette's (a phrase coined by Fraser Speirs), isn't necessarily relevant.