That is the Achilles heel of buying and owning a RAM. They are so heavily discounted most times, that they dive like a rock for trade-in value. That is why it is a heavy "stupid-tax" to not get the right one out the gate and trading off early is a heavy penalty.
literally just had this conversation with a co-worker who bought a tundra. North American manufactureres use the "inflated sticker price" model and then offer heavy discounts. In order to get a fair trade in on a newly acquired US brand, you need to know exactly how good of a deal you can get on it to narrow the purchase price / trade in value gap.
The guy with the tundra was talking about how great the re-sale value of his tundra will be and I agreed, until i told him that with his base model $36k truck would be a $40k stickered Ram. The ram should yeild a 20% discount ( at least 8k off ), with his tundra, he only got about $4k off.
Just for comparison, my wife and I are looking for a new SUV. Its between the grand cherokee limited or a honda pilot. The cherokee is about $45k on the sticker and the pilot is near $41K....similarly equipped. The pilot will likely only get us about $3k off ( so 38K plus tax ), the cherokee will get us about $7k off sticker ( so about $38k plus tax ). Will the pilot have a significantly higher trade in value in 5 years....maybe a little, but not by thousands.....same goes for the ram