Edit: oh and I just bought a 20 y.o. car. My way of seeing it is useful in this case because I add the (very high) assurance rate, repairs and gas to get a realistic price. I predicted a reasonable car life and compared it with the numbers for a brand new car.
In the case of your car, what benefits are there to the more expensive model? My iPhone X, those benefits are easy to describe, better screen, better camera, faster, better form factor. Amortizing to compare the relative cost between it an iPhone 8 and seeing that it's roughly $10 a month allows me to make an informed decision about whether those benefits are worth the cost.
In the case of your car purchase, if the car salesman says it's only $200 a month more to get the "better" car, are it's benefits worth that much to you? Is the more expensive car safer, more comfortable, and are those benefits worth $200 a month? How much do you drive a month? Do you commute in rush hour traffic, or drive on the freeway? etc. etc.
And if I'm wrong about 50% depreciation being typical over 2 years, I'm not wrong by much. There is not a huge difference between 70% depreciation and 50% in your monthly cost of ownership. Undamaged 64GB iPhone 6s are selling for between $230 and $310 on eBay, so that's 60-70% depreciation. On average the 6s cost about $20 per month.
Consider also the fact that the battery life will be substantially decreased from new and that most people wont be able to replace it themselves.
Something that is overprice is actually more likely to decline because 2 years from now its just a comparatively slow device that no longer serves as a status symbol.