<prompt> Human: Current situation:My wife is pregnant. We use one car work near each other, etc.My Audi has 80k miles and no warranty. I owe 8k more than its worth. I need to invest 1k in it for general maintenance. I also do a TON of driving, so its really an expensive toy. As much as I love it. My fear is my wife having the baby and the car breaking down, then us having to front the costs for repair, etc. We could afford new cars. We dont have a problem there. Were just not sure at what point you say its not worth putting more money into it.The new car were looking at is well within out budget and comes with free towing for 3 yrs and of course, has a warranty..Help?  <response>: When you own a car free and clear, the time to let go is when the cost of a single major repair equals or exceeds the cars book value.When you are upside down on a car, so you have to pay out of pocket to let go of it, you dont let go. You keep getting it repaired and you pay the loan down until your payoff amount draws at least even with the cars value.The worst thing you can do is roll a bunch of negative equity into a new long-term car loan which will keep you upside down for more years on a successor vehicle. A corollary bad thing to do is spend 8,000 to avoid a 1,000 repair bill, which is what you are contemplating or you wouldnt have written this post.You are stuck. Keep the Audi, make the 1k maintenance investment, and try to pay the loan down to even-with-KBB-value within 12 months. 