Here is my opinion, and I am not quite the mustache on this.
My story(pre stache): I bout a fully loaded mint, used Maxima with 27k miles for $22k from private party. Two years later 25k more and the car was worth in a private sale about $14.5k.
My wife bought a used 2011 civic with 6k miles off of Craigslist for $12.5k. Two years later and 15k miles, the car was worth.... pretty much the same from $10k-12k
Do I love my car? Yes! Was I a dumbass for spending so much? Yes! lol
Now to your case. If you want to drive a relatively "new" and reliable car about 2-3 years old, here are my choose for you. Civic, Corolla, mazda3, Elantra, and than you have a focus, Honda fit(ridiculous used prices in my opinion), and an accent. I would aim at $10k and below for the car with 30-50k miles. In the two years you own the car it should not depreciate more than $2-3k. You will need to do the research on the resale values, which car is most reliable, and than you will need to make sure you buy a well maintained car and negotiate a great price.
Out of all the cars I listed and owning the civic, I like the Mazda the most. I love the way they drive and look. The sedans are cheaper than the hatchbacks. But it depends on your opinion and probably the price.
However my advice is more for a car that you should keep for a long time. Buying a $10k car ties away $10k of investments, and buying a $3k car ties up $3k only. An that$3k car (if nothing goes wrong with it) will probably be worth $3k when you try to sell it again(unless you got some Saturn or something lol)
The Jeep is probably the worst thing you can get, especially in the city. Don't let the resale value fool you, it is actually not a good vehicle if not used for what it was built. Hard to park, uncomfortable ride, eats gas, just as fast as my civic, reliability issues(some year models are real bad), not a lot of space, noisy.
I think you need to spend some time and research you options. Hope I gave you some ideas and things to consider.
P.s
A $3-5k, 100k mile, well maintained, 2001 and up Accord,Civic, Corolla, and Camry also get my vote :). You can have a mechanic or dealership inspect the car for $100 or so prior to buying it.