I think while this is true, it’s the time you have to switch over is much smaller.
Windows XP kept being supported until 2014, and up to that point you had Windows Vista (2007), Windows 7 (2009) and Windows 8 (2012). That’s 7 years users had to move over.
Even if you consider something like Windows 7 with a shorter support cycle ending in 2020, you had Windows 8 (2012) and Windows 10 (2015), giving you 8 years to cave in and upgrade.
Windows 11 came out in 2022, and you have 3 years not to just upgrade the OS, but in a lot of cases your hardware too. I think this is why everyone is feeling the squeeze moreso than previously.
I had to do exactly this for a family friend in his 70s, it was a fucking nightmare. I think ultimately I caved and hotspotted it to my phone just long enough for it to be happy, and disconnected it while it was still loading the sign up page so it fell back to local account creation (at the time I didn’t know about a@a or bypassnro)