I see both sides of this. I'm a car guy, but having said that I have only twice ever bought a car new for myself (and both times they were deals through the dealer for loaner/specials).
My current car is a 5-series BMW, but I bought it used (it's a 2013) and is in immaculate condition. I also a) have enough knowledge to run and understand codes, and b) have a stepson who worked at a BMW dealer as a mechanic (between us we've owned something like 8 or 9 BMWs, so there's that) so there's very little that can't be managed. I have a payment, but it's nominal and more for convenience. My backup is a '99 Dodge RAM pickup that is in great shape, owned outright, but it's a work truck. I bought the BMW to allow my daughter to drive my "old" car, which I kept, a 2006 BMW X3 (see above), paid off long ago and worth more to me (and her) than I could ever get on the market or for trade, even though it's in very good condition. So for three cars, I pay a pittance for the car, I pay insurance (cheap because of the years and my driving characteristics), taxes (nominal) and upkeep.
Having said all that, it made sense to buy a newer model car for my wife, a long-term purchase. Rather than buy new, we went to Volvo, bought a car in off lease. It's got 70+k on it, but it's loaded and in great shape. It's expensive ($600 a month roughly) but I got a steal on the price (because of the miles) and I got the 10-year, unlimited miles certified warranty from the dealer. I hate the payment, but I'm buying more than just four tires and a motor for that and it's worth it to me. It's also a car I would drive, so if the fam situation ever changes, fuck it, I'll drive it. (I drove my old S60 - the car I had before the X3 - for almost 12 years; it was one of the two I mentioned above, a loaner from the dealer, and I bought it with 5,000 for about half of MSRP, and drove it all that time with only minor problems.) I pay more for the car, insurance and taxes than all the other cars combined, but it's solid, and she uses it to truck my stepson and my grandson. It's also the "family loaner" for when my stepson or daughter-in-law needs a car, etc. Worth every penny.