if you are in the 1500 market, good chance you can use something else - an SUV and a utility trailer, for instance. if you are in the 2500 market, you need a 2500, end of story. if they aren’t making many, and inventory got hit hard, then demand is “inelastic” and prices go up.
also if you are a consumer and you buy a used truck, down time is just an annoyance. when you are using your truck to make money, it’s lost work. so the 2500 fleet owners sometimes really are willing to pay for a new truck to minimize downtime.
i had a four door rubicon i bought in 2013 and in 2017 i traded it for my 6.0 2500HD crew cab WT 4x4. i had paid 35k for the Jeep brand new, and I paid 35k for the 2500HD. They gave me 30k for the Jeep with almost 50k miles, a dented front bumper, and smelly wet carpet. So I got a new truck for like 5k.
I can’t say my Jeep experience was entirely positive, went back and forth to the dealer over and over again for the same problems. But I ain’t complaining about the resale!