Cars
Friday September 12, 2025
It’s 8:52 pm on Thursday night, and this is the first time I’ve visited Substack this week. Buying a car demands a lot of your attention. I’m too tired to do anything but an essay this week. (Still not anywhere near as tired as Lindsay, who just walked in the door after her second multi-hour-long visit to the hospital today due to a lab error with her bloodwork).
Last week, the 2006 Subaru Outback I bought off my brother for $1,250 failed to start after a doctor’s appointment. After two hours, I got it towed to the mechanic by our house, who quickly diagnosed a faulty starter. $550 to fix. But more importantly, it clarified to me how vital it is that we have a second car. If Lindsay were at school with the good car and baby Potato had a health scare, a car that won’t start won’t cut it. So, I sold it for $1,000 and took an $800 loss. Price I pay for being too cheap to just get a real second car in the first place.
My first instinct was to lease, figuring we could pay a lower monthly payment and drive something new since we’re working towards owning our 2021 Subaru Forester. So, I started researching local lease offers and found a couple of options. My dreams of a $238/month 2026 Honda CR-V were quickly dashed, however, after a dealer conveniently failed to mention over the phone (even after being explicitly asked) that you had to be both a recent graduate and a current Honda owner to get the deal. We fudged around with some numbers for about 45 minutes and got to $275/month (before fees and taxes) if we put down $7,000 for a 39-month lease. That’s a lot of money to put down for a car you won’t own, so Lindsay and I walked away with the knowledge that if we’re getting another car to support a growing family, we definitively wanted something bigger than our Forester.
I realized when I got home that, despite writing about financial products and literacy for a living, car leasing was a pretty big blind spot. So, I did some research, fell down some Reddit holes, and came to the conclusion that putting down a large amount is usually a financially moronic move because your payment doesn’t actually impact the residual value of the car. Serious car people almost never do it. It buys down the monthly payment, but if you want to purchase the car at the end of the lease, you’re still gonna have to pay the full residual value.
So, I did some math, and that math sure did not math. We’d be paying $17,725 and we’d still have to pay $21,125 to buy the car at the end of the lease… for a car with an original MSRP of just over $30,000. And that’s before interest, financing costs, and warranties.
And that’s when I looked at our current loan for the Forester, calculated how much we paid for the lease, and immediately projectile vomited over how much we got taken for a ride by Cityside Subaru. So, I told the sales manager there that the $275/month deal on a 2026 Subaru Outback he was working on for us was no longer necessary.
I pivoted to used cars.
Turns out, there are many used cars for sale at any given time. I online shopped through literally thousands, getting increasingly precise with my filters to thread the perfect needle: Bigger than a Subaru Forester, fewer than 50,000 miles, less than $25,000, one previous owner, no accident history. I sent inquiries on dozens of cars, fully knowing the hell to which I condemned my phone and inbox. I emailed with dealers asking clarifying questions, I spoke to them on the phone at my own peril, and I eliminated cars due to distance, cargo space, and simple bias against American cars due to a horrible Chevy experience.
Given we’re down to one car that Lindsay needs to get to school, I really only had two days this week to look at cars. I narrowed it down to three models for Tuesday:
2024 Hyundai Tucson - Liked, didn’t love, and it felt like it would have similar cargo constraints as the Forester.
2024 Mitsubishi Outlander - Loved, very nearly stretched the budget to buy a 2024 Raillart for $28,500 because I was convinced it was meaningfully bigger than the Forester (I still don’t believe the internet telling me that it’s much smaller), and I loved how it drove. The weirdo salesman’s refusal to run any numbers for me until I made a commitment to buy merited a call to my dad to ask how common that was, to which he said, “Walk from that.” Five minutes of Googling revealed Automax Preowned to be an absolute scam show — could have saved myself a trip by looking into the dealer first, a note I made for the next day of driving.
2024 Nissan Rogue - Cancelled the appointment when I looked closer at the listing and saw it was a rental with multiple accidents reported.
The only positive takeaway from Tuesday was that I managed not to get ripped off! So, back to the drawing board, I extended the mileage and model range years a little bit since we really don’t drive that much, and this thing won’t need to be a workhorse. Suddenly, a few new models were in the listings: GMC Terrain, Ford Edge, Toyota Highlander, Hyundai Santa Fe, Kia Sorento, Kia Telluride, and a Range Rover Velar that my mom had to repeatedly stress the maintenance costs to get me to let it go.
I lined up three more for Thursday in Norwood, and two in Lynn for Saturday. Mom joined me in Norwood to drive some cars and offer feedback. Saturday won’t be necessary, because I made a purchase.
So, here’s what I drove. Tell me, what did I get?
P.S. It was a trick. We got a 2021 Kia Telluride EX that was not on the to-drive list because one damn good sales guy suggested I save time by driving their slightly more expensive used Telluride rather than go back to the other dealership to drive theirs again before making a decision. My mom and I both fell in love with the damn thing. I’m not ready to talk about what a rollercoaster it was getting this friggin’ deal done. But it’s done and we pick it up on Monday.