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So there's actually a forum where people analyze the resale values of the 5.5' beds and scream "Buy" or "Sell?"
My 2012 with 5.5' bed was bought for $29k (with $10,500 off MSRP) and traded in for $24k four years later. That definitely helped me buy the bigger one with 6.5' bed because I like to sleep in the back.
Around here, 5.5's are more in demand because parking can get a little difficult.