You have to look at it this way.
$400 a month for a car payment, so 4800 a year for 5 years. After 3 years maintenance on a new vehicle becomes a possible cost.
For your current car no matter what it is, maintenance will not even be close to that if you blow an engine, transmission, rack ball joints and tie rods all in 1 year and need to do the brakes with pads and rotors you might come close.
The issue alot of people find is based around the Sunk cost fallacy, looking at all of the money they have put into a vehicle and then somehow using that thought to justify buying a new one. i.e. "this car keeps nickle diming me to death". If you complete all repairs properly they should be fixed for the long-term, therefore your past investment into your vehicle should not influence any future decision making.
so 4800+ a year for a new car and the really expensive insurance, or maybe $1000 in maintenance for a used car owned outright. My personal route has been to stash $2000 for a winter beater every year and sell it on in the spring to make my money right back keeping my GP nice, I'll probably keep it forever as long as it doesn't end up as a mangled wreck somehow.
although i understand where you coming from and i also understand how great of an idea that may be you also have to remember that most $2000 cars also come with plenty of repairs needed in order to be safe/reliable...... where you live that may be a simple task and im only speaking on my personal experiance along with what ive seen available around me in that price range........ i also have a bit of a diff commute. i drive 150 miles a day round trip, so feeling confident that my $2000 car will get me to and from my destination and home without any hiccups or issues isnt exactly the best for me. however if your driving 20-50 miles round trip a day that might be exactly what you need but dont forget the initial costs to get the car safe... brakes, rotors, tuneups, fuel pumps, filters, bearings, fluids, ball joints, bushings, belts, pulleys etc....
as everyone knows when you buy a used car the rule of thumb is that your buying someone elses problem. reguardless of what may be wrong with it whether it be minor or major its still something that requires additional money to fix, new cars are not by any means worth the rediculous price they are asking for it now a days especially when the insurance to cover them to the banks standards doubles your monthly payment as apposed to a car you own outright. i love my grand prix treating it right in the city and on the highway averages me roughly 25 miles to the gallon which is plenty for me. if i wanted something great on fuel i would have bought another diesel (example.... a tdi jetta or something similar or another ram with a cummins) it really comes down to the owner and what they plan on using the car for, if they want something to be street and strip and get them to and from work reliably day in and day out then maintinace is the biggest factor, all cars require the same maintenance, the cost of those parts differ greatly depending on ur application high end cars require high end parts and just because a car is common or cheap to begin with doesnt mean that the repairs follow the same suit.
in the end it really all breaks down to the same...... a newer car is going to require the same wear and tear maintenance as an older car however a newer car will also require higher insurance and the parts (if its brand spanking new) will most likely only be available from the dealer ( and we all know how insane their prices are) however a used car that you own outright that you bough for $2000 is probably high milage, meaning that there are alot of things that have worn out and need replacing but were overlooked by the previous owner which adds up when your looking to make it safe and reliable. like i said earlier when buying a used car your buying someone else's problem...... there was obviously a reason that the previous owner wanted to get rid of it instead of fixing it and they 99% of the time never tell you EVERYTHING thats wrong with it.
if your comparing the out of pocket costs of fixing an old/used car as to purchasing a new one you have to realize although a newer car may be cheaper than fixing your transmission from the start ( lower down payment compared to trans cost) your overal costs are going to be much higher, and god forbid something happen to that new car that requires the insurance company to get involved. now your talking about higher premiums or the inevitable drop from their coverage. it really all breaks down to how capable you are for your regular maintenance and how skilled you are at examining a used car before you commit.
this is all my own personal opinion and based off of my own personal experience.