I buy 'new' cars when I see something nicer/better than what I have now, which is not often because my definition of better is not just newer and I cannot keep anything I find boring.
My best car was a Honda Integra Type-R DC2 (Jap import, 1996), awesome car, superb handling on Toyo R888s with the factory option suspension upgrades, reliably did 33-36mpg over a tank, unless you are absolutely hooning it (I did manage single figures for a tank on a trackday with it). Very little ever needed doing beyond regular maintenance, sold it because kids
and at 214k miles it was getting a bit smokey, new owner rebuilt the engine and its going strong.
Current family fleet is:
a little Honda Civic EK4 (Jordan, 2000), which was bought for the Mrs to get some NCB on her insurance and was oddly cheap to insure. currently on about 115k miles and just rebushed the suspension as it was getting sloppy, mid 30s MPG, get 2 kids in and it just works fine. engine spins to 9k so fun to drive yet not silly fast. We bought an audi to replace this as something a bit bigger to get the kids and crap in (civic does one or the other).
Four rings of the apocalypse! Needed/wanted something bigger, went looking at older Audi A6s, wanted to spend about 5-7K on something grown up looking. Ended up driving away in a 2004 Audi RS6, its behaved fine then was 'cuddled' by a lorry 2 weeks into ownership, bought another which has been nothing but trouble, engine has been out twice now, headgasket has gone again and will be coming out again. Its a matter of personal pride now, not rational thought, I will get the damn thing back on the road and reliable! then run it as long as possible.
Honda Insight 2002, this is my ultimate daily hack (I commute 88 miles round to work). £45 fills the tank, that gives you 550-750miles, road tax is free, parts are cheap (15" wheels, tiny brakes, 2.5l of oil in a change), its like a damn tardis inside, loads of room for my lardy 6'4" frame and its aluminium so (mostly) no rust! It is getting to an age (coming up 20yrs and 275k miles) where bigger jobs need doing beyond just servicing, brake and fuel lines, suspension bushes and dampers, The hybrid battery. These are all fixable though and not at insane cost if I do the work myself. I will keep this going until a cheaper suitable electric option comes along. I reckon it cost me about 12p/mile all in.