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I am also shopping for a used car. Our current (only) vehicle was purchased used in 2012. It's a 2011 Nissan Versa. We are searching for vehicles on cars.com to see what's available in our area, checking the safety ratings, and then visiting dealers. We obtained our financing through our bank so we can go in with a set amount that we want to spend and hopefully be in a better place to haggle.

I hear good things about the Hyundai Sonata. I tend to stay away from US cars just because in my lifetime we've had a fair amount of lemons from US cars. My Versa is okay as a commuter and in our four years of ownership, we have only had to do two major repairs (brakes and exhaust). Other than that, we replaced the tires once, the battery once, and have done routine maintenance. The Versa Note is not as good and is much smaller.

ETA: We rent cars a fair amount due to my husband's job, so when we purchased our Versa, we knew we liked it because we'd taken them on various long trips before. Right now we are looking at Hyundai Santa Fe sports because my husband really likes it and he's driving one for the next two weeks to see how it feels/drives.

Edmunds.com is a good place to do some research, and is an especially good site for pricing research (I’ve found it to be more accurate and easier to use than Kelly Blue Book, but that site is another option).

You don’t *have* to negotiate much if you don't want to. What you need to do is determine what your maximum price is, or terms that are deal breakers and just hold firm. Some dealerships have online departments too so you can do everything via email, which is a nice option if you don’t like pressure or confrontation. But really, if you do enough research to know what a fair/good price is and simply stick to that, you shouldn’t have to negotiate a lot – you just need to be able to hold firm and be ready to walk if they won’t meet you. Definitely check the car fax, which a decent dealership should provide you for free on any car they have for sale.

A few warnings if you are financing: don’t discuss what monthly payment you would ultimately like. Some dealers will turn the conversation that way because it takes away from both the interest rate charged, the total term of the loan and even the total price you’re paying. Shop around for financing deals. I was preapproved by my credit union but didn’t tell the dealer this. They quoted me 1% above what the credit union offered, so then I told them I was going to finance thru my bank. They suddenly “found” a financing promotion that was less % than what the credit union had offered, and much less than their initial offer. If you have decent credit, leverage that.

Many branded dealerships offer “certified used” programs. Some are better than others, so that’s another thing to research. You can also stack additional warranties onto a certified used warranty (at least both with Toyota and Lexus, so I suspect others as well), and I can tell you that for both those car companies the certified warranty is quite good and extensive. You can negotiate the price of the extended warranties, and I would suggest doing so.

I’m a big fan of buying certified pre-owned because you get nearly new cars and factory warranties for decent prices. I much prefer doing that to buying new, honestly.

We just bought a used car and first step was figuring out a list of possible options and then comparing the specs/ratings. We had a Consumer Reports magazine that was a car issue. Someone gave it to us so I don't know what the issue date is but probably in the last few months. We found that very helpful. US News also seemed to have decent information for researching.
We replaced my SUV but also did a bit of research on replacing DH's commuter car. We liked the idea of a Prius V because it gets great mileage but we could also use it as our car to take longer trips and do things as a family. It may be slightly over your price range though. We currently have a 2007 Corolla and it still is in great condition. It's a tight squeeze with rear facing car seats but should be fine once they are forward facing.

I drive a certified pre-owned prius that we bought from the Toyota dealership. I would definitely recommend going to the dealership and make sure it's certified pre-owned.

We aren't great at negotiating either, but I got the guy down about $4k, which I suppose isn't bad.

I love my prius and it has great gas mileage, but it would probably be a little tight with 2 car seats in the back. There is a larger version of the prius that may work, but not sure it would be under $20k.

Good luck!

@MUI831: It actually wasn't too difficult. I just told him flat out what we wanted to pay and he told me I was crazy and then he pulled his whole "let me see what I can do for you" thing and came back with $2k under the asking price. I told him I felt like it was still too high, so he came down another $2k and said that was the absolute lowest he could do, so we took it. It was pretty quick and painless.

And I totally understand, you definitely don't want a car that reminds you of your horrible ex boss! I don't like watching movies with Jason Bateman in them since my horrible ex boss looks kind of similar to him, so he's ruined forever.

@MUI831: We used the Costco Auto Program to buy our new Hyundai Elantra, and we were pretty happy with it. We got a decent deal with almost zero negotiating. We were in and out in just a few hours, which is pretty good.