I used to roll my eyes at my dad's frustration with his crappy old Windows desktops when I was a kid, but now I understand how he felt. I just want something that works and that I can depend on and use for basic tasks.
I switched to iOS shortly after because when using stock all my Google apps would constantly throw warnings that I had denied location services. Even apps like Gmail would prompt me with every new send.
The issues you mentioned like the soft bricking sucks.
On to iPhones. I have an iPhone 4S on iOS 9 too. It’s jailbroken because the sleep button doesn’t work so I needed a work around. It’s too slow for me though. Great if you don’t want to be able to use your phone much. Otherwise the wait to load apps and the limited or weird acting ram is annoying. Nonetheless when I want to try reducing my digital “addiction” I can get by using it. My friends find it too slow to even use for more than 2 min.
On the other hand, I also had a chance to use an iPhone 5 or 5S in the summer. It was perfectly usable. Fast enough and not that old of an OS (I think iOS 10) to be useless for downloading new apps.
But it's also important to consider that lack of Android upgrades are also slightly disregardable, as API and app level updates will exist for years, and the majority of older phones support custom ROMs. I understand how that's not the ideal use case for people, just providing my own take on things.