My Android phone is a 2016 model, the security update level is 1st of March 2018. :)
As far as ease of use goes, I'm not sure which action required fewer touches on WP8.1 and W10M (I've used them) than it does on Android.
From my time with the OS, I remember bugs with notifications and within the built in mail client and missing features (no quick search by contact name in dialer on 8.1?!, no swipe keyboard on 8.1) and confusing menus, and horribly designed settings pages where I wouldn't find the necessary option, because not all fits on one page, yet there was no scroll bar or any other indicator that there is more, and the "Resuming..." screen whenever I switched between two apps (I'm on a bus, listening to some music and playing Hearts; I switch to the music app to change the song - Resuming...; I go back to the game - Resuming...) and somewhat laggy UI (not too much, but by that time, Android was snappier).
In short, WP8.1 was a partly outdated, partly unfinished product. As for updates, there was one for WP8.1 when I just got the L640 and then not much. And W10M has been delayed and delayed, so I had to join the insider program to get it. And some things were better than in 8.1 and there were patches, but it was a beta and it remained a beta for the entire time until I gave up and sold the phone.
Never bothering to polish the current version and instead replacing it with a public beta? Not what I call good support.