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Resale value

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I think that the LR will fair better. I think that the SR will possibly run into more resale challenges as the average range of EVs slowly increases and costs decrease. A vehicle with 220 miles of range (when new and charged to 100%) might not quite make the cut in 5+ years? Others may argue that as more and more superchargers appear, range becomes less and less important. My 2 cents, but no one knows.

FWIW, I am expecting to get an extra $2K to $3K resale from my LR after 200K miles and 10 years. Call me crazy, but anyone can make any assumption and this is mine.
 
To get an idea, look into the difference between a 5 yo model S60 and S85.

Here I found the cheapest 2013 S60 $45,600 and the cheapest S85 $53,800. If you know the difference in value when new, you have an indication.
In my country NL I found the difference between new price of S60 and S85 to be about €16,000 (~20%) So the difference in resale value might have about halved in four years.
 
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LR will certainly have higher resale value, but the extra $9000 for the LR will depreciate faster than the rest of the car. The base $35k car with zero options will hold the highest percentage of the original retail price.
This has been true for ICE cars, and it becomes more true as the car ages.

I presume the Model 3 will follow the same pattern; and perhaps even more so since the range difference will drop in value as the cost per kWh of new cars drops.