You need a buddy. Someone who actually knows cars. Probably owns or works at a shop. He/she builds stuff. Has replaced their own brakes. Many times. Does their own oil changes.

Because here's the deal: There is nothing magic about the cars on a used car lot, or at a dealership. Most of them have been detailed, and pushed out into the lot in exactly the condition they came in. There is no "certified pre-owned". All that is marketing bullshit.

So what you need is someone who knows what to look for. They need to work with you to help you find the right car type, and then they need to come with you to look at a car. Bring cash.

Craigslist is actually better than dealerships, in this one instance. You find some anal dude who upgrades his car every 7 years or 50k miles, and you buy it from him. And cross your fingers.

Toyota Corolla. NO. Just... no.

Rav4. Excellent. My wife is on her third one. She LOVES them, and they work great, with little maintenance.

Subarus are great... until they aren't, and then the thing that breaks is FUCKING EXPENSIVE. They really are a crapshoot. I've got 10 or 15 friends who SWEAR by their Subarus (including me - Impreza Outback - and my sister - Forester, and my mom CV Legacy Outback.). And then I know three people who have been totally screwed... one was a brand new Outback that was just never right, the other two were ones that had major engine problems that would have cost $6k to fix. One of them only had the car for 3 months, and it only had 60k miles on it when she got it.

Insurance is nothing to worry about, unless you have been a bad, bad, person. Just call your insurance company, tell them the type of car you are looking at, and they can tell you about what you will be paying. Easy peasy.

Good luck. This is not going to be fun.