When do you give up your beater car for a new one?

When do you give up your beater car for a new one? Long story short I have a Toyota with almost 300k miles on it. I just replaced the transmission for 3k (kind of regret it) and had other problems come up. It works now BUT If something else comes up wrong with the car should I just cut my loses? My daughter was just born and would not feel safe driving her in it if I ever need to. Luckily wife ...

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