I have used Android phones for nearly 10 years now. My first Android phone was the first Android phone; the T-Mobile G1. I transitioned through a few different phones, and was appreciative of the developer community that kept these phones up to date long after the manufacturers had abandoned them.
I did get tired of replacing my phone so often, but the combination of rapidly improving hardware and unstable unofficial Android ROMs made it hard to stick with a phone for more than a year or so.
Then I bought the Nexus 5. I bought it at launch. It was a phone with high-end specs and a $400 price. Google provided three years of updates for their Nexus line, and I kept my Nexus 5 for just over three years. It had a mediocre (at best) camera, and poor battery life, but I loved that phone.
I tried switching to the Axon Pro, another Android with high-end specs and reasonable price. Sadly, it only received one update despite being ZTE's flagship phone, and it was much larger than I wanted my phone to be. I switch again in less than a year to the mid-range Samsung Galaxy A5. It's not a bad phone, but it's not great and I honestly don't know how long Samsung plans to keep the A5 updated.
So, what kept me from Apple all those years, and what has changed?
Price was a big factor. The iPhone is a very expensive phone. Unfortunately, if I want to repeat my "Nexus 5" experience, I would need to look at getting one of Google's Pixel phones and long gone are the days of Google's flagship phone costing $400.
From a personal perspective, most of my family use iPhones. While I wished people would transition to a cross-platform messaging system (like WhatsApp), Apple has successfully sucked people into the iMessage/FaceTime vortex. I don't like it, but not liking something doesn't keep it from being a reality.
Phone hardware is also not changing as rapidly as it once did. Keeping a phone for over three years isn't as crazy sounding as it once was, as long as the manufacturer is still supporting it. This fall, Apple released iOS 12 for the iPhone 5S, a 5-year old device! I have a family member with that phone. It still works great, and it has current software! I am not aware of a single Android device that has official support after 3 years, let alone 5.
One final note is that every time I have changed my Android device, the depreciation was significant. I am blown away by the resale value of used iPhones. Maybe in the long run the iPhone won't be as expensive as it first seems.
So, I'm giving the iPhone thing a whirl. I know there will be things that drive me crazy, and only time will tell whether this experiment will be a positive experience.