I think some here (and on Facebook) are missing the point of the writing. If you have the means to buy a new car free and clear and it fits your lifestyle this advise isn’t for you. Myself, I can’t walk into a dealer and lay down 40-60k so my 2-3yr old cars which I can pay off in a year suit me fine. (Although I am nearing a point where that 1yr is eroding to zero.)
Jared, thanks for the sound advise, but I think many reading already have either the fiscal responsibility and/or understanding of the money pit vehicles can be. 
I love the letters, they are good reminders of the ways personal finance is “personal” and to always be accountable for your own fiscal status.

Keep em coming…

Back in the ‘90’s, my neighbor at the time told me of a financial advisor comment he’d heard on a Saturday radio show.  The analyst was espousing the evil that is debt and said we ought pay cash for everything. The show host said yes, but we need to borrow for some purchases, such as a house and cars.  The analyst replied (paraphrasing), “A house, I suppose, but when it comes to cars, I’m afraid too many people are driving away from the American dream.”  Well said.

I used to keep cards until the wheels were ready to fall off. My wife drove an Avalon that was 17 years old and I had a Camry that destructed after 13 years and before an Infiniti that got to 230,000 miles. Now we lease - much more dependable and with up to date safety features. Yes higher cost but reliable and much safer. No more AAA calls.

Yep, have a 2003 Chevy S-10.  81K miles.  Just had the driver door re-hung….. now there’s little noise and feels new again!

We drove the also drove the wheels of our cars.  We have only purchased 3 new autos in the past 50 years and lots of used autos and pickups and airplanes. 
Two other things that really cost over time, are booze and smokes.  My sophomore year in college I counted up the checks I wrote for hooch—over $1000 in 1968.  That’s is about $3k these days.  i did get over it. 
However, for all my smarts (?) I did own two airplanes, then got smart and rented them for 30 years.  The docs don’t let me fly any more.  But from 1970 for about 30 years that was the only way to travel!

I Enjoy your wisdom.  Indeed I learned big lessons about money in the army.  Art museums are cheaper than the booze joints (I was in France) and attract lots of females.

Jim Johnson
Greenfield Mo

I did the math on new versus used cars.  On cars with good resale like Toyotas the cost per mile is the same on the new and old miles.  My most recent cars after we drove the wheels off the old ones are a Subaru Legacy and a base model standard transmission Toyota Tacoma.  We should get a minimum of 200,000 miles off each car and they are guaranteed to be well serviced.  I cannot keep up with our well off neighbor who still drives a wood paneled station wagon and owns 2 others for parts.  Her husband drives a Subaru Baja.  I do not live in a cheap neighborhood, I saw a Masarati recently.  I also see Teslas and such, but overall there are lots of CF’s on my street.  I still won’t buy the $3 drinks and am happily cheap, my big luxury is paying someone to clean my house and I don’t skimp on appliances or contractors.

The last thing I ever want is car trouble or tire trouble. And I want a nice, safe car. I put up with crap all my life, so now I don’t have to. But I had to for a long time.

Hi Jared, I like your comments on this issue. I would also say that auto companies would not be very happy to read this material. I am seventy eight years young and started driving at twenty, to this day I have purchase five new or used four cars in this lifetime. I loved the old cars of yesteryear when you could fix them just about anywhere when it became silent. Now I am not so capable as I used to be and motorcars have become impossible to fix in the back yard, but they do last longer if you take them to the dealership regularly as required, it does become expensive transportation. By the way my first car was a Austin Healy three thousand.

Jared, i agree and disagree with your car thesis.
Have you always driven a Toyota ?
If you have and that New car you speak of being a gently used is your second Toyota, I will agree you have won the car war.
I have wasted so much money on cars, and I have only purchased one new car in my life (in the last 40 years). The others all used.
Used cars break, even Toyotas and Hondas. That costs you money and time. With the second more valuable in my opinion.
Two years ago I finally woke up & decided no more depreciating purchases. I lease a 2016 Toyota SE for $195.97/month, all maintenance included (shouldn’t be any right? Well there are still oil changes tire rotations and a large one at 30,000 miles.  I did the math and I saved 40% on the normal cost of these done at a dealer.
In just over one year I will do a little car shopping online as I did with this one (didn’t spend one minute at the dealership until I agreed on the terms, all done via 4 text messages) and lease my next vehicle. Can I buy one of those other ridiculous cars? Of course but that’s stupid because I have 3 colleges to pay for that will give me a better ROI when I need someone to change my diapers in 40 years. Plus I get a new car every three years, my only cost is gas plus the $195.97/month. Pretty solid in my opinion.

Clue us in Jared, what’s the point of having a lot of money if you choose to live like a pauper?  I will die with substantial assets. I’m 68 and enjoying some of those assets.  I drive a Challenger Hellcat (absurdly expensive and fun), a Ford Flex (works well for road trips), a Dodge Pick-up (for hot-air ballooning), a 15 passenger van (for hot-air ballooning) and my wife drives her Buick. I also have a 48 Chry Cpe and a 49 Chevy truck.  I have 4 hot air balloons, all for fun, no paid rides.

The point is, the value of money is the enjoyment it brings.  Numbers in a ledger are nice but at some point, I want more.