I don't have the knowledge to give a full post, but I absolutely hate car repair. And if you buy a used car, there's a good chance that someone is selling it because it has maintenance issues. This happened to me, and no matter how many times I took the car to the mechanic it just kept having problems.

On the other hand, new cars have a huge extra price tag just because they're new. So the classic advice is to never buy a new car, because the moment you drive it off the lot it loses a ton of value instantly.

Here are a couple ideas for how to handle this:

1. Buy a car that's just off a 2 or 3 year lease. It's probably in great shape and is less likely to be a lemon.There are companies that only sell off-lease cars.

2. Assume a lease that's in its final year. (at http://www.swapalease.com/lease/search.aspx?maxmo=12 for example) Then you get a trial period of 4-12 months, and will have the option to buy the car. This way you'll know if you like the car or not and if it has any issues. The important thing to check is that the "residual price" that they charge for buying the car is reasonable. See this article for more info on that: http://www.edmunds.com/car-leasing/buying-your-leased-car.html

There are a ton of articles out there on how to negotiate a car deal, but one suggestion that might be worth trying is to negotiate and then leave and come back the next day to make the purchase. In the process of walking out you'll probably get the best deal they're going to offer. You can always just come back ten minutes later and make the purchase--they're not going to mind and the deal isn't going to expire (even if they say it is).