I've only owned one brand new vehicle in my life, and at just one month old, it was stolen and totalled. I took such a beating from the insurance company, I've never since wanted to risk that huge depreciation incurred by driving a car or truck off a lot.
I typically have looked for a car I like at about three years old and low mileage, which has gotten easier with the internet and the ability to shop from home at any distance I'm willing to fly to to get what I want.
I had a 94 Isuzu Trooper for 18 years, loved it, kept it looking and driving like new, then after production stopped in 2002, started having trouble finding parts and service for things beyond brakes, batteries and tires, which actually was seldom, as it was very reliable. The last straw came when the gas tank rusted out from driving on the beach to fish two or three times a year since I got it. I had to have a gas tanked shipped from a junkyard near Seattle to Virginia. I sold my old friend.
If I find a vehicle I really like, I try to keep it going, but the one thing I won't put up with is rust, because that's a futile battle once it starts.
My current daily driver is an eighteen year old BMW 740il. I've had it fifteen years and I love it - plenty of power, quiet, roomy, simple dash, loads of luxury features with PUSH BUTTONS, no *&^%$%^touch screen. Driving to Florida, it gets 27 mpg. I'm at about 125K miles, and this will be my forever car, Lord willing and some fool doesn't t-bone me. I would like to have, and can afford, a new all wheel drive mid size SUV to go back on the beach to fish, but it seems like they're all an over gadgeted, jewelry box/video arcade, instead of a tough, utilitarian vehicle I wouldn't mind taking off-road, capable of pulling a medium sized trailer or bass boat and getting dirty now and then. They're all styled Corporate Average Fuel Economy compliant jelly beans or else a madman trying for the "Dune" look styled them with the the back of a shovel and a hatchet. They might be more fodder for the soccer moms to sit up a bit high and peer over the steering wheel while not having a clue where the four corners of the vehicle are, but their gadgetry, smashed roof lines that only a midget can climb in and out of easily and bunker-like side windows aren't for me. I'll probably shop for something ten years old or thereabouts to find a utilitarian four wheel drive.