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.