I cannot fathom paying significantly over $100 for a phone, especially one you carry around all the time and beat up and will be almost worthless in a couple years even if you treat it very carefully.
The only impetus for upgrading a phone for me is if it starts failing at being a phone. I upgraded my old SE to the new SE when it was on steep discount earlier this summer solely because my old one took a few tumbles in its life and was dropping nearly every call.
Other than that, the phone wasn’t slow at all. The rear camera was acceptable. The battery life was fine. If it wasn’t dropping calls I would still be using that phone. In a lot of ways I miss it, primarily the size and the light weight compared to the new SE, but the design flaw of getting dust under the front camera lens pushed me to the new SE ultimately since it made the front camera next to useless after a year in a pocket. It happened in my iPhone 5, my 5s, and was never fixed in the SE1, lending further creedence to my theory that engineers at apple don’t use the products they design, or at least certainly not for the typical length of time that an end user would before being handed the next generation device to use from work, before most critical issues crop up.
The longevity of recent phones is a huge contrast from the early days, where an iphone 3g would struggle to function on the mobile web or basic apps compared to the 3gs, but those days are long gone. iphones have been more than powerful enough for 99% of peoples use cases since the iphone 6s. A 6s or SE1 is still a perfectly performant phone today.