Ask Jack: Trading in Your (Chance at a) Chevy for a Cadillac-ack-ack?

Way before the book Rich Dad, Poor Dad existed, I had my own financial angel and devil on my shoulders in the form of my grandfather and mother, respectively. Granddad retired at 54 and lived more than four decades in perfect comfort based on the investment decisions he’d made prior to retirement. My mom is… well, let’s just say she didn’t retire at 54.

Mom always had champagne taste and a debutante’s contempt for anybody who did not. When my grandfather decided to buy himself a Cadillac shortly after retiring, my mother told me, in quite snippy fashion, that it was “a used Cadillac, like what a loan shark would drive.” I don’t know what I thought I was going to find in Granddad’s garage when I got there, but the six-month-old ice-blue Eldorado Biarritz that he’d actually bought wasn’t it. He took me to the grocery store in it. When we went to the register, he took out a coupon book.

“Granddad,” I asked, “why do you use coupons if you have a Eldorado with a stainless steel roof?”

“Johnny,” he winked at me, “that’s why I have one.

Shortly afterwards, my father bought a Town Car. It was brand new, which pleased my mother. But in my heart of hearts I always liked Granddad’s Eldorado better, all the more so because I knew he got it cheap. Every time I manage to buy something outrageous at a steep discount, I think of my sharp-dealing grandfather and his delight at never paying retail for anything. Which brings us to today’s questioner, who is considering following in the old man’s footsteps, after a fashion.

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  • SCE to AUX Over the last 15 years and half a dozen vehicles, my Hyundais and Kias have been pretty cheap to maintain and insure - gas, hybrid, and electric.I hate buying tires - whose cost goes by diameter - and I'm dreading the purchase of new 19s for the Santa Fe.I also have an 08 Rabbit in my fleet, which is not cheap to fix.But I do my own wrenching, so that's the biggest factor.
  • MaintenanceCosts '19 Chevy Bolt: Next to nothing. A 12v battery and a couple cabin air filters. $400 over five years.'16 Highlander Hybrid, bought in 2019: A new set of brakes at all four corners, a new PCV valve, several oil changes, and two new 12v batteries (to be fair, the second one wasn't the car's fault - I had the misfortune of leaving it for a month with both third-row interior lights stealthily turned on by my kid). Total costs around $2500 over five years. Coming due: tires.'11 BMW 335i, bought in late 2022: A new HID low beam bulb (requiring removal of the front fascia, which I paid to have done), a new set of spark plugs, replacements for several flaking soft-touch parts, and two oil changes. Total costs around $1600 over a year and a half. Coming due: front main seal (slow leak).'95 Acura Legend, bought in 2015: Almost complete steering and suspension overhauls, timing belt and water pump, new rear brakes, new wheels and tires, new radiator, new coolant hoses throughout, new valve cover gaskets, new PS hoses, new EGR valve assembly, new power antenna, professional paint correction, and quite a few oil changes. Total costs around $12k over nine years. Coming due: timing belt (again), front diff seal.
  • SCE to AUX Given this choice - I'd take the Honda Civic Sport Hatchback (CVT). I 'built' mine for $28777.To my eye, the Civic beats the Corolla on looks these days.But for the same money, I can get an Elantra N-Line with 7-speed DCT, 201 HP, and good fuel economy, so I'd rather go for that.
  • Kwik_Shift_Pro4X '19 Frontier Pro 4X. Next to nothing. All oil changes are on schedule. Got new tires at 60000 miles. Still on original brakes at 79000 miles. Those are due soon. Brakes complete estimate $1000 all in.
  • Dr.Nick The cars seem really expensive with tight back seats and Cadillac was on the list of the highest price gouging dealers coming out of COVID. I don’t understand the combination, shouldn’t they be offering deals if they are not selling?