Updates for Android continue to be a huge problem.
Android OEMs have historically been terrible at releasing timely updates (it can take months), releasing updates at all (particularly cheap Android phones get EOLed long before an admittedly way more expensive iPhone would) and such updates aren't typically pushed in the same way.
One big problem with Android is the way driver updates work. It's a nontrivial process to add hardware support for a later Android version because of the Linux roots and having no stable ABI.
I think back to how Windows has changed over the last 2 decades. Once Windows updates were all paid and people would hang on to old versions of Windows forever. Microsoft eventually realized this was a problem for them so paid upgrades aren't what they once were.
Additionally, driver instability used to be a massive problem on Windows. Microsoft to their credit spent a lot of effort improving their driver situation to isolate drivers and have a stable ABI. Windows is way more stable than it was 20 years ago.
Even OSX has adopted user space drivers (DriverKit).
By the way, the above reasons is why some at Google have pushed Fucshia as essentially an Android ecosystem and architecture reset. It's been close to 10 years now. I don't see this going anywhere despite billions being poured into it at this point.