I upgraded from a 4 year old Moto X to a Pixel 2 in January to facilitate a switch to Project Fi. The feature I like best on my new $550 phone is the location of the fingerprint sensor on the back. It is a design that every phone should copy. But, other than being faster and having a better camera, it's still just a phone so I am struggling to be happy about the price that I paid for it.
I don't like the XL sized phones, so if i could redo my decision today I would buy either a Nexus 5 or a first gen Pixel. Either one would have to be used. I feel like a new phone is worth around $300 or so because they just are not significantly better than our old phones. What happened to Moore's law? Why aren't new phones twice as fast and half the price of old phones?
Regarding Apple versus Android, the main reasons for using Android are the wider choices (phones and apps) and relatively lower prices whereas with Apple, if you're already using their ecosystem, then it's probably easier to stay put. Also, as someone mentioned earlier, if you like having the latest phone, then Apple's resale value is a big benefit.
FWIW I own an Android phone, iPad Air, Dell Win7Pro laptop, and MacBook Air. I like each one for its uses, and I will give props to Apple for the quality of their iPads. If anything happens to my Air, I will definitely replace it with another iPad.