Jeep Wrangler or help me buy a new car!

[Don Julio Anejo]

Well, so I'm finally financially stable enough to do something about my 1994 Honda Civic that has enough scratches and peeled off paint on it to qualify as a prop on STALKER: Shadow of Chernobyl. I've been absolutely enamored with Jeep Wranglers for a long time, so I'm basically 100% decided on a base model automatic 2 door Sport version (one of these little buggers).

However, I've never bought a car before, my parents always paid cash for newish used Civics, and all of my friends either lease, or bum rides from parents/other friends, so I can't ask anyone in real life.

So, in short, how does the process work? I've got decent credit (~730, will probably jump another 10 points after I pay off a Visa card that's had a balance on it for a while), and I'm looking to finance.

Is there a specific way you haggle with dealers? Is new worth it, since Jeeps keep their value extremely well (a new one will be about $23,000 without tax with automatic transmission and AC, and 2008-2009 models sell for $15-16,000)? Otherwise, I'd be looking at 2008 models and later, though my dad is adivising I don't consider anything more than 4 years old for reliability/maintenance reasons (neither of us is a car guy so a loose pipe or battery connection warrants a trip to the mechanic). If I see a used car listed at, say, $17,000, how much can I realistically get it for, assuming I'm not a middle eastern bazaar trader and am fairly average at haggling? Is there a specific time that's better for making actual purchases, say end-of-month?

Finally, is there a huge difference between bank or dealer financing, or between new and used financing?

I'd be really grateful if you guys could answer any of these questions.

[Trianas]

I’m a diehard Jeep guy and am a bit bias on the topic so keep that in mind as you read on!
I have owned 2 Jeeps recently- the first one my wife bought for me as a surprise while I was in Iraq, unfortunately, she went to a shady rip-off type dealer and they saw her coming a mile away…. Anyway the jeep was a 1991 and had a lot of mechanical issues and the electronics were shot (not because it was a Jeep it just was not maintained well) after doing about $200 worth of work I sold the jeep for a profit of about $1000 (they hold value real well)
With all that said- I bought my new jeep and it is a 1995 and I have done a lot of things to it as far as lift kit, larger tires, changing the gear ratio and on and on…. I wanted something I can swim in the mud and I made it into a beast… that is my cup of tea and not for everybody… even if you prefer to keep it as a stock jeep and just for daily driving it is a GREAT vehicle to invest in…
As far as which year model you want to buy and the age of the vehicle it will depend on what you would like to get out of your Jeep…
If your credit score is about 730 you will have more room to haggle. The example used jeep for say $17,000 can be a great buy, and you could possibly haggle your way down to about $15,000- Another option to dropping the asking price would be to ask for accessories for the Jeep…
The best advice I can give would be go in there knowing the bluebook value of the jeep tell the Dealer you will buy this jeep if he is willing to meet YOUR offer, if not tell them you will look somewhere else and if they can meet it to give you a call- they WANT and NEED to sell you that Jeep! don’t go in there feeling like you’re asking a favor from them…. Tell them your offer and they can take it or leave it… (you don’t have to be rude but be FIRM) they don’t make a living on missed sales.

Good luck and I hope all this rambling has helped a bit…