At some point it will plateau the way PC hardware has, and new major OS versions won't be as much an issue.
[0] https://arstechnica.com/apple/2017/06/review-10-5-inch-ipad-...
Windows rarely felt that way. Linux does feel this way most of the time if your needs are "tech saavy". If people could register that a recent eOS, arch+gnome3 or mint+xfce can make their machine fast, cute and even more functional than ever ... I try to show them but they fall into the grumpy reflex (ewwww that key doesn't do what it did, delete linux !)
The PPC to Intel migration was handled beautifully. Rosetta was straight up magic. It "just worked" and was around a few versions.
Intel Clover is not even a different architecture, it's still x86. Makes me wonder if (and believe that) Microsoft could've made this transition more graceful had they wanted to.
Complexities aside, Apple keeps things running. I have never had to worry about my MBP simply failing to work due to OS compatibility issues.
Of course this machine was expensive when new, just like Apple-branded hardware is expensive. Sometimes all that money buys you something worthwhile like your 7 year old MBP or my 13 year old T42p. Other times it is just a lot of money down the drain like I expect the recent touch-strip-addled MBP series or any machine which has consumables glued in-place to keep pesky users from getting a few more years out of their investments.
There are certainly many more moving pieces in the Windows realm though, simply considering how backwards compatible Windows tends to be, how much it has changed in the past few years and how many different systems it runs on. I'm very curious to know what the reasons behind Windows CU's incompatibility are.