Yeah, at ~$15k, I’d shoot for a new car and figure out how to make up the small difference. Besides the obvious advantages, not least of which is a full warranty, it’s a hell of a lot easier shopping for and buying a new car for a great price without haggling. If all you want is a simple, basic compact car, it should be easy to walk out the door under $20k, maybe even well under that, depending on your wants and needs.
Once you figure out the make/model you want, go to truecar.com and get a ballpark idea of the “true” price, but DON’T sign up for their service to contact dealers for you. Find all the dealers in the general area and go to their websites and try to get the email address and/or phone number for their Internet or Fleet sales rep. Email address is preferable, but gather whatever info you can find for each dealer before you start contacting any of them. Some you’ll have direct email addresses for, some will only have some sort of “Contact Us” web-form or dealership-wide contact email, some only the rep’s phone number will be on their site. Some might not even have any of the above, and you’re probably better off just skipping those unless the other options are sparse.
Start in the order given above, contacting those where you have the direct email address for the Internet/Fleet sales rep. For each dealer, see if they have their inventory listed online, so you can see if they actually have the make/model/color/options car you want, and how many of them they’ve got. (The more of the exact same they’ve got, the more eager/willing they’ll be to move them quick.) In the email, tell them the specific make/model/color(s)/option(s) you want, mention that you see a few in their inventory, and then say that you want their best possible “Out the Door” price including Dealer AND Destination fees. The only acceptable costs/fees excluded from their quote should be Tax/Tag/Title. (Two “D’s” included, three “T’s” excluded)
Prominently mention that you are similarly contacting various dealers for their best “Out the Door” price, AND that you will be paying with a cashiers check and will NOT require financing through them. Once you get your insurance check, figure out how much more you’ll need and secure the funds yourself, whether through your bank/credit-union/etc. You might also mention that you are purposefully NOT using a car buying service like Truecar/Costco/AAA/etc, and you hope that they’ll appreciate your direct and straightforward approach by being direct and straightforward with you. (They’ll be happy to save any fees they’d have to pay for those services.)
Hopefully you were able to get a few direct email addresses to send the above email to. Give them a day or so depending on what responses you get, then move down the contact list to the dealerships that only had a general “Contact us” web-form and see what you get. Depending on the results, then move on to the dealerships where you were only able to get direct phone numbers to the Internet/Fleet sales rep, and be well prepared to verbally tell them the same terms you wrote in the email.
The key is letting them know that you are contacting various dealers for their best prices, are aware of how the game is played, and won’t need financing through them. At that point, they’ll know to give you the best possible price and have a shot at getting the sale, instead of letting one of their competitors get the sale. They make enough money on the Dealer fee and whatever Incentive fees they get from the manufacturer, they just won’t be hitting the jackpot when you walk in the door.