I am in the camp of owning and driving a vehicle until it is more expensive to repair than buying a new or newer one.
My first car, which I still have, is a 1972 Chevy Nova. When it was my daily driver, it was really more trouble maintaining it than it was worth, but at least that is where i cut my teeth on being able to do minor to intermediate repairs. I learned how to remove and replace an engine, transmission, and how to do other things like tune ups, changing the oil, etc. Now, it is a weekend cruiser I drive every now and again. It gets people talking and it is fun to drive in a nostalgic way, but I would sell it in 2 seconds if it was my only vehicle. Old muscle cars are cool to drive (more properly, to be seen driving ) but as daily drivers, they suck ass.
My second car was a 1966 Pontiac Lemans (or lemons!). That continued my forced knowledge of car repair. I mailny bought it because my best friend at the time had a 1967 GTO which looked almost identical, except for a few trim changes. I had beefed it up with a 1970 GTO 400 V8 bored out to a 413, and changed the 2 speed auto to a 3 speed turbo 400, and upgraded the axle to a 12 bolt posi traction with 4:11 gears. The thing was fast, but the engine was far more powerful than the car was designed to handle, so you guessed it, I spent almost as much time under the hood as I did driving it.
From those 2 cars I learned one truth: don't get them unless you love working on cars. In my older age, I hate it, and I am debating on selling my Nova. I also learned that trucks>cars, if you don't care about gas mileage. They sit higher, are designed to tow things, and as such if you drive them like a car, typically last longer than a car.
I've bought only 1 brand new vehicle in my life, and it was a 1995 Dodge Dakota sport, my 3rd vehicle. I owned it from 1995 to 2000. It had a peppy 4 cylinder with a manual and 3.90 posi gears. It moved like a V6 S10 of the same era. I loved that truck, and never had an issue in the 5 years and 75,000 miles I owned it.
My 4th vehicle was a 1997 Ford f150 XLT extended cab. Probably the nicest vehicle I owned. It was optioned to the max, and I bought it in 2000, with less than 15,000 miles on it. Except maybe the Lariat or Eddie Bauer editions, it was the top of the line for 1997. I drove it until 2013, when it had 220,000 miles, when I was in an auto accident that totaled it out. I bought it back with a salvage title, with the intent of repairing it, because it seemed it just needed a new bumper, grille, and driver fender, but I later found out it had a bent frame. I ended up signing the title over to a auto body guy, who did some paint and body work on my Nova. He probably fixed the frame, and repaired the damage, then flipped it. That truck was very reliable, and other than maintenance repairs like brakes and minor stuff, the only major issue was I had to replace the transmission at 200k miles. That was pretty expensive at $1800, but cheaper than buying a new car. With used cars, it was better to go with the devil I knew. Months later, I had my accident.
My current vehicle and daily driver is a 2006 Ford F150 XL regular cab. I bought it immediately after my 1997 F150 was wrecked through my credit union. It only had 43,000 miles at the time and the paint and body looked fine. It currently has 110,000 miles. It has been a good truck in the last 6 years I've owned it, but earlier this year, the engine went out. Let me tell you, that was an expensive repair bill! I bought a rebuilt 4.6 V8 from Jeggs for $2700, and hired a guy a friend referred me to install the engine. He only charged $800, so it was a lot cheaper than buying a new truck, or go with a used vehicle, which really means you inherit someone else's problem.
Had I not had either the connections for repairs, or ability to do them myself, I probably would have gone with buying a Toyota something, maybe a Tundra, and traded it in once the warranty was over!