my guess is that if he is looking at a 4x4 4 door truck that isnt a penalty box he is already gonna be damn near $40k anyway... if you want a warranty and you need to finance, new is the way most people go, and for good reason, but have you priced new trucks? you want something with power windows and 4 doors and 4wd, you are looking at pretty close to 40k, in every flavor every manufacturer offers, silverado, f150, expedition, cherokee, tahoe, whatever. So if you want a new dual purpose rig you are gonna put 30k miles on a year, and you know youre gonna spend between $35-40k for it, mileage would make a big difference over the next 5 years. 150,000 miles at 20 mpg would be 7,500 gallons of fuel. 30 mpg is only 5,000 gallons of fuel. At $4/gallon thats $10,000... so if you had to spend $10,000 more initially and you ended up with a better tow vehicle to boot, it kinda pays for itself. Not to mention if its a diesel, the residual cost will be there when you resell. Realistically, around here diesel costs more and diesels generally have higher maintenance costs due to greater oil capacity, frequent fuel filter changes, and now, with DEF and etc, its even higher. So that might be a wash. But if this jeep could really get 30 mpg highway, that is pretty substantial savings over the lifetime of the vehicle.