I would gladly pay extra for a XS or XS Max because I upgrade annually and iPhones hold their resale value well. Proportionately, the cost to own a XS or XS Max won’t be that much more than a XR. The one advantage the XR has is that 128GB is the perfect size, but I don’t think the difference in price is as drastic as people think if they factor in resale value. Then again I do expect a price drop of ~ $100 for the next generation (not necessary imo, but sales say differently) which may depreciate this generation quicker than usual.
You may have a point about resale. I keep mine for about three years and then pass it along to my wife. She couldn’t care less as long as it makes and receives calls and texts and gives good directions via occasional GPS usage (Google Maps).
Mentally, I just can’t come to grips with a $1000-plus smartphone. Perhaps one day. Like I’ve said, I’m usually on my MacBook Pro or iPad Pro.