When the Car Tells You It's Time to Trade, Listen

Dear Car Talk | Oct 18, 2016
Dear Car Talk:
I have a 2005 Mini Cooper S Convertible with about 99,500 miles. A few thousand miles ago, the transmission started acting up. It has a hard 1-2 shift and is slipping between 2-3. I took the car to AAMCO and to the local Mini dealer, and both said that I need a total rebuild -- cost would be $5,000 to $7,000, depending on which place I use and whether I want a warranty. In addition to the transmission, the Mini shop says I need several other repairs (strut mounts, engine fan, etc.). All in all, I estimate that it would cost at least $8,000 to put everything (that I know of) back into working order. The Blue Book value on this car is around $5,000 ... not taking into account the failing transmission.
For this reason, I am thinking that I couldn't even sell it to anyone as is. This car is paid off, and I do not really want to have a new car payment. I am concerned though, that even after putting in $8,000 for repairs, something ELSE will break and cost a few thousand to fix. I know that pretty much every car purchase is a horrible investment; how do I determine whether it is LESS horrible to fix up the Mini and keep it, or to buy a new(er) car and have to make payments? I know I could get "a" new car for relatively little money, but I'm not the type of person to drive just "a" car. I want "the" car -- the one that fits my personality and style. Should I trade in the Mini and take the $2,000 or whatever a dealer will give me? Or should I just keep it and drive it until it falls apart?
-- Coop
I think you've already "driven it until it falls apart," Coop.
You are very fortunate, really. Very few car owners get such a clear message that it's time to walk away from an old car. Usually, it's $1,100 here, $1,700 there, $750 a few months later. But you've had a car-repair lightning bolt come out of the sky: Spend $8,000 or get a new car.
So get the new car. You got 11 presumably happy years out of your Mini. Say "thank you" and trade it in. Take the $8,000 you would have spent to fix the Mini and take the $2,000 the dealer will give you in trade, and you've got a very substantial down payment on whatever you want next.
And for $15-20 grand, you can get a Mini Convertible that's three to five years old, if you want another one. Or look for something else that tickles your ball joints.
This is a blessing, Coop. The skies have opened, a rainbow has appeared and the junkyard beckons. Go toward it.