The bottom line is unless you have money to burn, trading in your vehicle is almost never a good deal financially.

I just sold my '07 2 door sport stick and bought a '13 4 door sport auto.
For shits and giggles I asked the dealership what they would give me on trade, and they came up with $12.5k.
I sold it 9 days later, private party, for $16k.

 

The only one that you listed that seemed high to me was the 08. I bought my 07 Sahara (78k miles, 2.5" BB, new 35" trail grapplers, hardtop) for 20,600 after taxes from the dealer. Which was actually a good price for where I live. All goes back to the supply and demand I guess..around here there is low supply and high demand.