Story:
Had a 1995 Jeep Cherokee passed down to me in highschool, drove the shit out of it (250,000+ miles), loved it, got rear-ended, car got totaled. Insurance company gave me ~2,800 or so for it which I used as a down payment on a used 2003 Honda Accord ~$12,000. I had my first big boy job and paycheck and thought the car was cool. Fast forward to now: I setup low payments (~$300 a month) and currently owe ~$7,500, I live in the city and park on the street which lends to chips, scratches, broken windows, keying, etc..., I do not want this vehicle anymore.
Solution:
Sell the car for around the amount that I owe and purchase another Cherokee for cash. I've learned in this time that I could care less about the style/speed/whatever of a car and only value it as a means of transportation, nothing more. I hate the stress that comes with owning a "nice" car and want to rid myself of it. I have ~$5,000 bucks or so that I am willing to shell out for another Jeep.
Problem(s):
Car has some scratches / dents / body damage. The biggest issues are a recent keying mark, a dent from a frisbee and the passenger side body kit has broken off after running over a curb and bending my fender. This is where I need advice:
Should I:
Pay to have the body work fixed, get the car detailed (or detail it myself) and try to sell it myself?
I realize this will net me the most money for my car but I fear that I will not be able to sell it.
Try to trade my car with a dealer that has a Jeep like the one I want?
Not sure exactly how this goes down. If my car is worth 7 or so and the car I want is worth 4-5 or so, how does a trade-in work? If I went this route should I fix the car up first?
Get raped by selling it to Carmax?
I realize this is probably a bad idea but I'm throwing it out there.
Thanks dudes. I'm also really trying to eliminate car payments as I may be changing my life in a way that I have less income to work with.




