I mean, I dunno how things are on your side of the pond, but here this would preclude a contract that is more expensive for otherwise equal condition, usually meaning a higher total cost of ownership.

I also tend to throw on a custom rom anyway - my four year old midranger is on the current version of Android. More and more devices also tend to get supported for longer, so that's worth considering.

Also, out of date and brand new have gotten more and more meaningless for smartphones. I've got a processor fast enough to run everything I do seamlessly, a nice and sharp display, and a battery that lasts me a day. That's about the same I'd have with a current flagship.

I mean, it's your call, and I don't really care what kind of phone you use, I just don't think it's quite as black and white as you paint it.