Yes, I'm sure such exercises work fine for any real-life OS: if you take, say, Ubuntu 1.0, then run all the intermediate upgrade steps, you'll eventually end up with an up-to-date system as well.
The real question, though, is: after a successful OS upgrade, how many of your installed apps still work without issues?
On Linux, this varies: popular source-available apps tend to do fine, whereas less-common and proprietary (not to mention expensive!) apps fail after even minor updates, with no other resolution than 'ask your app supplier to do better', which is not always an option due to said supplier being too burned-out, bankrupt, or both.
On MacOS, apps generally seem to have a 2-5 year lifetime, after which they break for various (often minor) reasons. Resolution is as per above, and often unavailable due to suppliers disappearing or giving up because of to the relatively small size of the MacOS market. iOS has similar issues.
On Windows, you can generally continue to use even the most obsolete apps for 10-20 years, and often even longer. Of course, traumatic generational changes (obsoleting DOS or 16-bit WinAPI apps) still take their toll, but compared to other operating systems, this happens a lot less often, and migration tooling is often available.
The entire WoW64 subsystem is the epitome of Microsoft backwards compatibility fervor.
WoW64 makes 32-bit programs work under 64-bit Windows by providing an entire 32-bit copy of the 64-bit operating system, and then transparently redirecting reference calls made by 32-bit programs to them instead.
It's simple in design, brute force in execution, and practical in results. I hope Microsoft never changes their backwards compatibility philosophy; other operating system vendors should strive to be like them.
Not only that, they built an entire x86 and x64 emulator into Windows for Arm, so that (for example) if you install Parallels on a M1/M2 Mac and run Windows on it, you're getting the special Windows for Arm build, but many of your apps will still run because of the built in emulation of Windows.
It's just crazy compared to how much software just completely breaks between different macOS releases with no recourse, or have to be recompiled and reinstalled from scratch on Linuxes. Microsoft's bad at a lot of things, but they deserve a huge amount of credit for their backward compatibility on Windows...
While you’re right that Linux doesn’t have the binary compatibility Windows does, I think you gloss over the advantages of source availability. Having the source lets you patch bugs and avoid the (impressive and commendable) hacks described in the article.
It’s also worth noting certain Linux releases have extended support so you continue to get security updates without upgrading (a strategy Microsoft also uses).
Still, it is a downside of Linux and macOS compared to Windows.
