There seems to 6 main schools of thought on this, and I don't think there's a right or wrong answer. Obviously, you tailor your purchases to fit your needs. That being said, what seems to work the best for you, over all of the years you've owned cars?
1) Lease - i.e. my brother; pay the depreciation for 3 to 5 years and turn it in when you're tired of it and want something else.
2) Buy new, sell when the warranty is up - usually 4 to 7 years of ownership. When the warranty ends, make it someone else's gamble.
3) Buy new, sell it after ~10 years - after 10 years it's time to move on while it still has some value, sell it and let's get something else.
4) Buy new, keep it until the wheels fall of and it's worth $1,800 - i.e. my dad; still drives a 1995 Dodge Ram 2500 he bought new in December of '95, has almost 400,000 miles and isn't worth jack (and might die any day).
5) Buy 1-4 year old CPO car, feel it out until the warranty is up, sell or keep it depending on how much you like it.
6) Buy used, never new - buy a 2nd hand car, keep it as long as you want and then sell when you're tired of it or it won't run anymore.
Your dad’s truck,
Is it a Cummins?
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