Can you offer advice in buying a car in my circumstances?

I am currently in the process of purchasing car #5. Before you offer advice, please consider my detailed circumstances.

Cars #1–4 were basically “disposable” cars for me; each lasted about 1.5 years. They were Hondas or Toyotas from 1994 or 1995 and cost around $2,000. (All were purchased in full from a private seller in an ad.) I drove them until their needed repairs exceeded their value and then moved onto the next disposable car.

Now that I’m almost 23, it’s getting kind of embarrassing to drive a car that looks so old, and I think it’s about time I have a car that will last me longer than a year and a half and that I won’t be ashamed of.

I would be satisfied with a Honda Civic, Honda Accord, Toyota Corolla, or Toyota Camry (or something similar!) from around 2001 or so. At least something like that would look respectable and be more reliable than the ones I’ve been driving that are twice that age. I’d prefer that the car has less than 100,000 miles on it and not require any repairs.

Now, even though my previous cars were somewhat embarrassing-looking, the nice thing about them was no car payments! I paid the $2,000 in cash and didn’t have to worry about monthly payments. I realize that I’m probably going to have to finance something as new as 2001. I really would prefer not to do this, especially because that would mean I would have to purchase from a dealer, which would be much more expensive than a private seller who posted an ad. And it’s just so much nicer to not have to worry about making monthly payments.

I also don’t know how much I should reasonably be choosing to spend on a car at this point in my life. I could afford a down payment of about $2,000. (I am a first-year grad student, and my stipend is $30,000 per year. Since I just graduated college in May 2008, I have no savings yet.) Obviously, I’d prefer to just purchase another $2,000 car and be done with it, but that would likely result in yet another embarrassing-looking car, and I really think it’s time for me to move up from that.

Considering all of these factors, what is reasonable to do in my situation? Should I buy a real car, suck it up, be an adult, and start making monthly car payments like everyone else? Is having a non-embarrassing-looking car worth the monthly payments at this time in my life?

If the answer is yes, what is the best way to go about this purchase? Would it be possible to find a 2001 Honda or Toyota for a reasonable price through a private seller?

Or should I go to a dealer? I went to two dealerships today just to look, and the 2001 Hondas and Toyotas they had were listed as being $9,000. I do NOT want to have $7,000 worth of car payments—no way. The MOST I would probably be willing to go for is $5,500 (that is, $2,000 down and $3,500 financed), but I would still prefer to buy a car under $4,000. Is it possible to get a respectable-looking car for this price? If so, how and where?

Also, for those of you with experience at car dealerships, if a car is listed as being $9,000, what is the most you can bargain it down to?

If you have any additional avenues for car purchasing to suggest, please do!

Thank you for reading this very long explanation of my car situation, and I am very open to advice in how I should handle my next car purchase!