A word about Chrysler or Dodge minivans vs Toyota’s or Honda’s. Yes, the latter two are more reliable, however when bought used they are much more expensive for age and condition. I find the Chrysler’s more comfortable with better ergonomics and much more useful since I have always hauled cargo and people. Chrysler’s stow and Go seats have the competition beat by a lot, and the Japanese vans don’t have enough legroom for me.
Since I do most of my own work, the price outweighs the repairs. I have also never lost a transmission on one, but I change the transmission fluid and I don;t wait until the tranny is acting up to do it. It’s too late then.
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I agree with @oldtimer-11.
My Dodge Caravan is about 20 years old, now. I purchased it new. I have had virtually no problems with it. Of all the many Dodge cars I’ve owned (3 Aires, 2 Intrepids, 1 Neon, 1 Stratus, 1 Spirit) I’ve had very few things go wrong and never engine or transmission problems. That’s why I kept buying them, because they were reliable.
Used Dodge Caravans are plentiful and a bargain.
CSA
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Two quite different examples from my surroundings…
One my coworker runs Caravan with 215K miles he bought with around 100K miles: still going “OK-ish” on original engine/transmission.
Seeps oil left and right, but not to the point where it is too big of a deal yet.
Transmission developed a little bit of “lurch” between 2nd and 3rd, which is still tolerable.
Sure, he replaced a number of wear&tear items, but basics are OK.
The only complain he has is that old plastic clips/connectors/wires/etc… tend to break the moment you touch them.
This guy is a DIY-er, so he was cherry-picking car he bought used.
Another friend of mine bough a Caravan with 95K miles from the dealer and after inspecting with his fellow mechanic.
This guy has ZERO knowledge on cars and looked for the cheapest price at purchase as the only factor, he is not very big on maintenance either.
At 120K miles: transmission is dead-dead, he disposed of car.
To some extent, buying used car is a lottery, and if you are to win, you either have to have skill yourself or you have to have a trusted mechanic, but it boils down greatly into how well prior owner[s] maintained the car and for you to assess that in short time you spend on purchase.
Buying new is a very different thing as you get to maintain it yourself, and generally car will be in far better shape if you planned keeping it for a long time right from the start.
Good advice. Used cars can be a bargain, are a bit of a gamble, have to be selected carefully as you have outlined.
I generally buy used cars. Most have half their miles used and half remaining, yet cost 70% to 80% less than when new.
I wasn’t even looking for a car when I saw that Grand Prix (picture at left) on Craig’s List. It sounded too good to be true, so I had to go check it out and have a little fun. I had never even sat in one. I took it for a ride and I ended up writing a check, practically pocket change. It’s like new! I will probably drive it for 10 years.
CSA
As others have said, there are tons of used cars that don’t have such obvious issues. All used car purchases should be preceded by an inspection by a qualified mechanic, but just to put this in perspective, consider this scenario:
If you were looking for a potential mate, selecting one from the waiting room at the local VD clinic is probably not a good idea. Yes, some of them may wind-up testing “negative” for communicable social diseases, but when you start with the people in that waiting room, your potential for getting a “deadly” mate is definitely higher.
My advice is to cast your net wider, and to seek vehicles that don’t have such obvious flaws–and then to have the “finalist” inspected by a mechanic of your own choosing.
Once I was given similar Grand Prix as a loaner and was really pleasantly surprised 
As for me, I like to buy fairly low-mileage used cars . . . under 100K. The price doesn’t have to be rock-bottom, but fair. If I get the sense the car was reasonably well-maintained, I go for it. If something seems odd, I walk.
And once I get it home, I do ALL the maintenance, because I treat every freshly purchased used car, as if the previous owner never did any kind of maintenance. Sure, it’s a little time-consuming, and costs some money in parts, but my labor is free, and my method has worked for me, so far at least
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for last 2 cars, I was getting 82K / 105K as mileage, but they were both a solid base to work on
doing the same: replacing all fluids, belt/plugs/wires… was REALLY surprised how much all that things really take money-wise once I decided to keep a log when getting an old Nissan Sentra for my daughter…
still, worth every penny, as if you pick that car carefully as a candidate for restore, then make things right, it runs like new 
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Thank you.