@kjofkw There are now several good Android phones available for less than $300. We got Motorola Moto G5 plus phones from Costco and Amazon for less than $250 each, no contract. There’s now a newer version, I believe, but the G5 plus has been very reliable and performs well. A key for me was that Motorola committed to delivering regular OS updates for the phone. I was on Windows phone for a few years, but coming back to Android, I was impressed with how much better the OS is now–the Google integration is pretty impressive. I just don’t understand why people drop $800-1000 for a new iPhone every two years.
After a while, the new updates won’t apply to older phones, so that can be a real problem, and it also gets to a point where repairing them is not cost-efficient. I usually keep my iPhones for about 3 years and use a Speck or Tech 21 case and a glass screen cover, so the one I’m trading/selling looks like new and commands a decent price. I’ve got an iPhone X right now and love it- everyone else in the family loves their iPhone 8+s.
My S4 mini lasted 4.5 years. DH has a S5 and is miserable that the microphone is shot and can’t be repaired. We don’t like planned obsolescence!
Currently, this appears to be true only for the Android One version of the Motorola X4 (Android One branding requires monthly security updates). Since Lenovo acquired the Motorola phone business, there have been complaints about updates being inconsistent or lacking, unlike before.
I generally keep my phone 3-5 years. Usually the “final straw” that causes me to upgrade is that one of my most-used apps has a useful update that is not available for my old device.
I hate paying to replace a phone, especially due to the cost. (I still can’t believe people are paying $1000 for an iPhone X!!) And I hate that Apple makes the iphones essentially become obsolete because you just can’t update to the latest iOS and then an app stops working, etc.
That said, I usually replace about every 3 years. And then I buy the last generation phone that has been discounted.
I just switched from my samsung to an iphone. The differences I see - facetime, better picture storage and the battery actually lasts. My phone is essentially my work computer, I use it a ton. I replace it probably every 2 - 3 years.
“the battery actually lasts” 
…for now.
Most new phones’ batteries will last better than an old phone’s battery that has had many 100%->0%->100%->0%->… discharge/charge cycles.
I am still rocking an iphone 6 with the original battery on 10.x.x and won’t update it to 11.
My daughters just got the iphone x and I gotta say I’m jealous. It’s a sweet phone with monster battery life and a very good camera. Even the notch doesn’t bother me.
I’m okay with my phone until it stops working - hopefully it will last a bit longer.