I did that with the first car I bought. Way back in the early 90's, I got a car that was a bank repossession. I don't remember how many miles it had on it, but it wasn't many. I do remember that it was only 6 months off the car lot and the cost was significantly less than buying a new one. One advantage of growing up in a small town, the president of one of the local banks went to our church, so the parents let him know we were looking to get a car for me to go to college and he told them that the bank was in the process of reclaiming the car. Worked out nice for me, but I always kind of wondered about the person that couldn't keep it.
I always carry full coverage since the late 90's when my Jeep Wrangler died from mechanical issues. Having to come up with money for a replacement vehicle with little warning convinced me it was worth keeping full coverage. I may not get much from the insurance, but at least I'd get enough for a down payment. (Like this time).
You might be surprised. The sticker price on my Encore was $25k and they came down to $16k before I paid my downpayment.
I actually did compare apples to oranges, as well as Granny Smith Apples to Red Delicious, and even plain apples to apples.
The dealerships that had cars in my price range to pay cash, all of them were 8 year old or older, with 170k miles or higher. Most of them were 10 years old or older, and with more than 200k miles to begin with.
When I was looking at fleet and end-of-lease vehicles, the prices went up to $12k minimum, and even those had more than 40k miles on them and they wouldn't go past 54 months on the financing.
The next bracket started at $15k and had 30k miles or less, and were 2014 and 2015 models, but the initial sticker price was significantly less than the MSRP on the Encore.
Comparing Encores specifically, the least expensive one I was able to find was $19,800, and was a 2014 model with 35k miles.
So, what I saw was I could
1) pay cash for a clunker and accept that I'm going to keep paying maintenance for a while on something that probably won't be worth a lot.
2) Accept that I was going to have to finance, and either A) finance a little less money for less time or B) finance more money for longer, both options which came out to really close to the same payment (All of them were between $250 and $300 per month).
3) get a slightly used car that was initially worth less and pay a higher monthly rate
4) get a slightly used car with comparable initial value and finance a higher amount
5) get a brand new car and finance a lower amount for a longer time.
I'm not saying that there wasn't a better deal out there, but in the immediacy of having 4 days to find a replacement car, I feel like I got a good deal.
One of the things that limited the available pool of acceptable cars is the fact that I drive between 800 and 1000 miles every week. So, any car that wasn't rated at 30 mpg or higher I did not even consider. When I first got to the dealer, they showed me a nice used car that actually was cheaper than what I financed, with relatively low mileage, but with an estimated mpg of 18. My little Vibe was getting 35-36 mpg and I was paying between $200 and $250 a month in gas. So, if I cut the mileage in half, that doubles the cost of gas, and adding $200 to $250 a month in gas is almost a complete car payment in itself.
Yeah, I have lived in 3 or 4 states in my life. Some of them didn't have property taxes, but had high sales taxes. Some had low sales tax, or no sales tax on food and clothes (or even no sales tax at all) but had high property taxes. One had property tax on housing, but not cars, but had high registration taxes on them. It seems like in general, the taxes I paid were fairly consistent across the years, it was just a matter of where, when, and under what reason it was collected. That being said, I've never lived directly
in a major metropolitan area, though I did spend 15 months close to Minneapolis/St. Paul. (About 30 miles south of the Mississippi creek. It's not a full river up there

)
All I can say is "See the CarFax"! And if they don't have one, or won't show it, move on.
I don't know about other states, but here in Arkansas, we have a "lemon law". If a new car has to go back for mechanical repairs more than 3 (?) times in the first year (maybe 18 months), or the total repairs are more than a set percentage of the initial value of the car, the dealer is required to replace it with a different car or refund the amount paid. That does not include repairs for accidents or normal wear and tear. But if it consistently has issues, then there is a resolution available. I have never had to deal with it, but I had a friend in college that got a brand new truck for high school graduation, and before the summer was over it had been in the shop for transmission problems a couple of times and it seems like it also had an engine problem. He wound up with a year newer model for the same payment.