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So it seems like your inner problem definitely has to do with emotions rather than being a true need for a vehicle.
My dad has an 03 4Runner that he is sentimentally attached to. He's owned it for 14 years yet it only has 45k miles. Needless to say, I think he wants to keep it forever. The reason why he likes it is simply because he didnt like the ride of the current 4Runners. It's also our only SUV with the rest of our cars being small Eco Cars so it's actually nice having when you want to switch it up for a change. But like I mentioned, it is a low-mileage car and he drives maybe 3000 miles a year or less, so he never gets tired of it.
There have been occasions when he wanted to sell it or trade it in. He has put it on Craigslist maybe two times and always finds a buyer. His co-worker always tells him that he'd buy the car as soon as my dad is ready to sell it.
My dad really likes the new Highlander and the new Lexus RX. It crosses his mind that he can easily sell his 4Runner and get either of those two.
The reason he doesn't is because there is really no need for him to get a new car. His situation may be different from yours in that he has grown kids fresh out of college so his only reasoning for getting a new car would be "because it's nicer."
But I think the reason why he's so emotionally attached to his 4Runner is because it has satisfied his needs for so long. Since he has never had the need to get rid of it or change to another car, he perceives his 4Runner as invaluable.
The real reasoning behind sentimental attachment is fear. It's the fear that you will make a huge mistake by getting rid of this said object. It's the fear that the new car you get will not make you as happy as the car it replaced.
I sell cars for a living and people trade in their cars that they've owned for 15+ years. None of them get super sad or anything, but sometimes I do get the occasional "I feel like crying because I'm replacing my car." And this is the fear kicking in. Apart from the fear of a big financial commitment, most things going through these people's head are "what if my new car doesn't last as long as this one." Or "What if I don't like my new car as much as my old car I kept for 20 years?"
But you know what? These people let go. And they let go because they need a new car. This same person can also be thinking "I won't see an expensive repair bill or be stranded because of the new car warranty." Or "This new car is so much safer for my baby/family" or "This new car has so much more space that I never had in my old car."
And that's where I realized that a lot of people can be sentimentally attached to their cars, and the way to let go is by having a true need to.
Tldr; Letting go of a car can be hard but it is made possible by having a definite need to.
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