Thus the "expensive" iPhones are $250 or less per year. And they are, in my opinion, usually better than the Android equivalent.
You might say; "but what if I have the same upgrade cycle with iPhones". Well, then you can have a look at what a used version of the last gen iPhone costs. Where I live; it is something like $100-200 less than what it was new. That means; some people are having the newest version of the iPhone for only $100-200 / year. That is, at least, roughly the same price as your are getting (or better, depending on resale value of the specific Android phone), but with the newest version of a more premium product.
In other words. You might be getting ripped off at $260. It all comes down to money over time, not amount at a defined moment, unless the amount is prohibitive.
When it was time to upgrade, it apparently also became time for apple to jack up the price of their flagship to a thousand bucks and I just vehemently avoided that out of principle.
Looking at alternatives,the Galaxy seemed like a reasonably similar premium (not polished software fosho) phone, but sticker price was similar to iPhones. However thos things go on sale a lot. Nabbed a S9 few months after release for 500 and looks like it'll last me three years at least. Super happy with the hardware (and software actually) as well.
The only "flaw" in your logic above is that in principle an iPhone probably can last 4 years but that's not constant - models from them are sometimes just not as reliable (we talking 4 year reliability vs 3) and it's not just a thousand dollars, it's thousand and tax and bells and whistles (which for apple is always more). Plus you now have a premium phone that you better don't break or scratch (if you want to sell) or you're out a very large number of Benjamins.
Don't get me wrong, I am writing this on a Sony Android phone, which I expect to get 0 dollars for if I try to sell it. But from an economic perspective I don't think there is a clear advantage to Android devices.
In your opinion, the iPhone is better, so it's OK that you're spending more, but it's weird to say someone's getting ripped off by buying an excellent one year old phone for much, much less.
The money over time argument rarely works out as better for a more expensive item. Anecdotally, the people I know that buy a brand new flagship do not wait four years between phones. The ones that are OK with a one year old flagship are also OK with a three year old one. And even if they upgrade more often, it's just so much less expensive (over time.)