When and why did you decide to be done with beater cars?

I got teased in my Camry a couple months ago when I drove 3 coworkers to lunch, it was hilarious. "Nick, how did you go from driving a Tesla to this?" "Why doesn't the seat belt work?" (Turns out one doesn't work), "My window doesn't go down", and I've had the same steering column meow since I bought the car almost 7 years ago. Another time we went to lunch in it, 25 miles one way, I got asked "Are we gonna make it?" :ROFLMAO:

I now try to guess which days we go to lunch together and drive the Grand Cherokee on those days.
That's called character.
I went from a 97 Honda Civic beater in 2020 to a 2018 VW GTI and am now selling the GTI and will go back to a cheapish beater. I've always driven nice cars so my first real experience with a beater was that Civic. I bought it from a friend for $600 and got it fixed up so it was a decent little car. Interior condition is really important to me so I made sure it was super clean inside. I sold it because I was ready for a different car. Now I am going back to a sub $5k car again. I love the GTI but car payments suck and I can sell it for a lot more than I bought it for. In our current economic climate, freeing up an extra $366 a month feels like the right thing to do. There seems to be plenty of Civics, Accords, Camrys, and Corollas for sale in the $3500 range that I can buy and drive. Having a reliable backup car (my 4Runner) makes me feel better about having a low buck car. Also, new car project (if you know what I mean).
I'll be turning 59 in few months and have always bought cars in the <5,000 category.

I did try to buy a new car once but I guess my credit history was not good enough. In the long run it was a blessing, never had to deal w/ monthly payments.

At this time, I can afford a new car but not interested in the current stuff. The main focus on the screens, and the nannies which I hate.
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The mistaken idea that a cheap purchase price saves money is just that. Cars have a specific lifespan, and purchase price is only about 1/3 of the total cost of ownership. Add in that old cars don't have a long expected lifespan and the price reflects the expected service life.

A well purchased new car is only about 10% more expensive "per mile" than a used car.

Yes and no. I've seen new or new-ish cars break down and require pretty expensive repairs. Having a new car does not insulate one from unscheduled downtime. They are generally a poor value unless you have to have the best, which they are.

Lots of 5-7 year old Mercedes, etc. getting towed away. I would rather deal with a 10 year old Chevrolet.

Your point has some validity and is understood. There is a point where getting a 20 year old rust bucket ends up costing too much.
Car repairs are no fun. New car payments get old quick. New cars need new tires just as fast as used cars with fresh tires. Insurance costs, convenience, fears over door dings, depreciations, one new vs multiple beaters, risks with buying old lemon vs new with warranty, inconveniences of breakdowns, etc etc etc…

One of the best things about buying used that I like is that there is generally plenty of data out there on how reliable that particular make and mode vehicle is likely to be, and with things like carfax you can do your best to avoid buying abused vehicles. This helps swing “luck” in your favor of avoiding a heap of junk money pit.

Great points.
In 2018 I had a 2006 Nissan Sentra with 206K miles on it.
It needed front brakes and rotors plus struts all around.
I was going to fix it but one day the drivers door would not open.
That did it.
All fixable but probably $2000 at a shop, I dont wrench anymore.
The same day the door broke I went to my local Hyundai dealer and got a brand new Elantra GT.
The junk yard got the Sentra and paid me $205.
We got rid of the beater New Beetle last week. It went into limp mode for no apparent reason, and my daughter had to call me for help. So, she took my 233k mile Camry to dance class and I hopped into her 108k mile Beetle and drove it home with no problems. Restart seemed to reset it.

This car has been constant work, so my wife agreed it was fine to say goodbye. I put it up for sale for a junk price and it sold within 24 hours.

The only bummer is that it drove perfectly during the test drive. Even to the point where I second guessed selling it. You have to be able to trust a car and that was not possible anymore.

My daughter is enjoying her new to her/cast away by me Camry and I found a 15k mile Rouge that makes me happy. No more beaters in our house.
I've been driving new cheap cars for a while now (see sig). But I do occasionally buy a beater to have some fun. I like the idea of being underestimated. Driving a $3k car (pre-covid) with no debt outside the mortgage, wife and I with what I consider good jobs. But many people would assume you don't have 2 pennies to rub together.
I have owned a car dealership for nearly 20 years and have access to new cars with a free tank of gas.

The funny thing is I never drive the new stuff. I sell a lot of late model vehicles but our two dailys now are a 2005 Ford Freestyle AWD with only 63k miles and was maintained exclusively at a Ford dealership, and a 2012 Mitsubishi i-,MiEV that received a brand new lithium ion battery with greater range (100 miles) shortly before I bought it from a customer who had two of them.

I have about $4000 in each one. Having said that I drive about three to four different vehicles a week to get them to the repair shops, emissions testing, inspecting the overall condition etc.

Before the kids went away to college we sometimes kept the most fuel efficient vehicles with the best histories for around three years and broke even when we sold them. Before she got more into a keeper mode my wife sometimes went through close to a hundred vehicles a year and I drove about a hundred fifty myself. Even now I drive every single vehicle we retail and if it isn't up to my standards, it goes back for what it needs.

The only new vehicle I ever bought was a red 1994 Toyota Camry coupe. 28 years later it's still on the road with over 400k miles. If I weren't in the car business I would probably own that and a red 1996 Miata. Plenty of great vehicles out there but I prefer cars that are easy to work on and figure out.
Bob 5150. I have been a car guy for many decades. I used to buy new and keep cars a very long time. I have bought used sports cars and recently bought a couple used vehicles that i really like as the cost was acceptable.
Your problem in my opinion is two fold. Your car selection is pretty awful unreliable cars and the age of them is way too old.
Ram and dodge are lousy bets and cavaliers are just poorly built as well.
My advice is to buy a mid size suv or mid size car around the year 2010 or even a couple years newer if its a price you can swing.
Your goal is highly reliable and simple cars that can be driven many miles with few repairs other than tires , brakes , battery , exhaust or maybe a timing belt replacement.
Toyota makes some fantastic small suv and cars that would be a lot lot more likely to provide years of service without major expense.
Corolla , camry highlander rav4 tacoma would all be great choices.
Three years ago i found my sister a 07 highlander with 150 k miles for 6500 dollars. New tires and new brakes and battery and a fresh timing belt were all done by the cars first owner. All toyota service center work as well.
My sister has had about 1000 dollars in repairs in 3 years and 65 k miles inc oil changes and wipers and a couple oil leaks and cooling system service with belts. The highlander looks great and drives great and is reliable and very very useful in snow and for all her driving.
I have friends with ten to 12 year old camrys and those cars also just run and run.
You need a car that has had good regular service.. and the timing belt / brakes / tires air cond are all functioning. That will give you a car you can own 5 or maybe even ten years without constant huge money for repairs.
The car you buy must must have service records that show the oil changes have been performed at say 3500 to 6000 miles with regular service. You dont want a used car that was in a serious accident or was a salvage title in any way.
These days i would budget 8000 to 12000 dollars and dont be afraid to pay a mechanic to go over the used car and give their opinion of the car condition and needed repairs. Buying a car with 150 k miles is not terrible. But anything over 200 k miles seems it might be more risky and better be on the less expensive range.
You may need to look over 15 or even 30 cars to find one that seems like its in good shape and a good bet to purchase.
The only american car that might be a reasonable choice would be a mercury grand marquis or ford crown vic around the model year 2010. Those cars are easy to service and are very well built. They did great at fleet use and police cars and cabs.
The v6 chrysler minivan can also be quite durable and is capable of high mileage and being reliable. Rust is a problem if you see it under any of the cars in more than a minor way.
Hope you find a great toyota and drive it a very long time .
I have bought two beaters in my life when I took a job in 1997 that required a 130 mile round trip daily.
Both "Beaters" were "Toyolets"; a 1987 Chevy Nova, and the second was a 1996 Geo Prizm.
After I polished off the Prizm (on advice from my mechanic) I took another tact and created my own beaters.
I did this by keeping a newer vehicle , as well as the work car. When I purchased a new car for myself, the vehicle replaced was delegated to work status.
I did this with a 1995 Ranger PU, and a 2000 Taurus (both purchased new by me.) Took the Ranger out to 165K, and the Taurus to 275K.
In November of 2013, I purchased the Accord in my signature as a leftover '12. I knew that I needed it to last until my retirement (April 30, 2015.)
Put 72K on it during that period, and decided to keep it post retirement. Still have it.
I've had beaters,good used and now I have a 2019 V.W. bought new with a 6 year,72,000 mile warranty. I maintain it by the book except I do many short trips.V.W says 10,000 miles on the oil.I've read a lot on oil dilution so I do 5,000 on the oil and most importantly do oil analysis. It shows low to moderate dilution.My advice would to use all resources if buying used,inspection,car fax,oil analsis.In my case analysis makes my car a better vehicle for me or the next guy,just by the knowledge, piece of mind.
I have driven and bought new cars since my high school days into my late 30's.

With maturity, priorities, and new vehicles that are of questionable quality and cost that insults even a moderately intelligent human, I now prefer older used vehicles with one goal - to get me where I need to go. I don't care what it looks like or how fast it is. I'll take the status quo funds and put them towards retirement or basically anything else besides some overpriced hunk of failure.
I'm starting to get sick of these older cars.

The Grand Cherokee needs work, which is to be expected after 8-9 years and 134k miles. But it's kind of annoying, and it's expensive. Am I really saving much over buying new? Not so sure.

But the car market is too wild right now, and I just need to slow down, gone through too many cars this past year.
In the last year, I'm $5k into the Grand Cherokee with a suspension refresh, new tires, and new brakes. It's going into the dealer for a transmission service and the headlights fixed on Thursday. I'm hoping that's it for along while. I was thinking of getting rid of it in a year or so, but it looks like I'll need something to tow a trailer from time to time.

Thinking I'll just give my brother the '00 Camry. It's tired and seen better days.
I've always had good luck buying 3 to 4 year old cars with ~100k on the clock with full service history. I then keep these maintained until I decide I fancy a change.

Unfortunately, my current employer who provides me with the option of a company car and fuel card, or allowance and fuel card have strict requirements on what you're allowed to drive for work purposes which limits me to buying a car under 1 years old and I have to get rid of it before it turns 5.
Beaters are okay until they are no longer reliable. Not including a serious accident, it's time for one to go when you stop trusting it, it nickels and dimes you to death, it needs major work worth far more than the car, or rust takes over.

Even if you choose to replace, say, the engine at $5K on a car worth $2K, then you can expect the transmission to go at some point. Do you spend another $5K for a replacement?

Once you've been stranded on the side of the road the first time, start looking for another vehicle. Upon the second time, stop looking and replace the beater.

You can always make the case in your mind (and the old Car Talk radio show said the same thing) that it always makes more sense on paper to keep pouring money into a beater, as opposed to buying a new car. The reality is that at some point throwing away more $$$ is a waste, or the car simply cannot be repaired. For every vehicle, especially cars as opposed to light trucks, important parts become unavailable, and then you have no choice.
My 2001 Honda Civic is certainly a beater. It’s got a battle of rusty bulge going on beneath the driver’s door. But It had a nasty electrical gremlin a year ago that seriously made me consider jettisoning it. The ECU told me it was a failing crankshaft position sensor, but it took me a while to finally figure out it was the camshaft position sensor. During that time I replaced the crankshaft sensor and two camshaft sensors.

The first camshaft sensor nearly drove me into psychotic madness. When the OEM crankshaft sensor failed and then the aftermarket camshaft sensor failed, I was livid. Turned out in a desperate last ditch effort, to avoid buying overpriced covid cars, I swapped the napa camshaft sensor for a better made in Taiwan sensor, and the car was fixed. Amazing a new aftermarket napa part can suck right out of the box.

But since then the civic has been flawless and cheap. The perfect money saving beater that I have no stress getting dings, exposing to corrosion, and deterring theft.