I’m kind of in the same place , I like nice cars but I try not to spend too much on them .
The most I ever spent on a car was the £14K my first W124 cost me 21 years ago , that car lasted me 11 years and I covered 200K in it before selling it for spares .
I also spent five grand on a W114 back in the early 80s , kept it a similar length of time and also got over 200K out of it .
In each case I felt I got my money’s worth , although I’d have felt hard done by if something catastrophic happened early on .
Most cars I buy nowadays tend to be at the pocket money end of the scale : my 500SEL cost me £1300 and lasted me 5 years without missing a beat , covering 100K in that time , I gave it away due to rot underneath which was going to cost a lot to fix . I’ve had three 190s , the most expensive being the 2.6 bought for £500 , all were good cars , still have the third one , bought for £250 , after a few months running it was evident from coolant loss that there were CHG problems ; I sourced a known good 2.3L engine for £200 and fitted it myself , also upgrading brakes and fitting a taller diff .The diff , bought for £75 has turned out to be a duffer so I’m looking for another ( well actually I’ve found one , just need to collect from the Black Isle . So far , between buying , the engine , diff , brakes , new rear springs , tyres , battery , exhaust , Oris detachable towbar, the car owes me a little over a grand but is still worth more than that . Again I’ve had the car 4 or 5 years and had good use out of it ; I have new front wings , rear wheelsrch repair sections, so at some point will get the bodywork sorted as it is sound underneath.
I can’t remember ever selling any of my cars for money , I usually either give them away to friends or family , or swap for something interesting; my troublesome S203 was swapped for my SL , which I’ve now had for 5 years but since none of these cars have a lot of money invested, I can walk away from them at any time and can afford to just go out and buy another . I was offered a W140 a couple of weeks back , tempted but said no as I really need another estate car , been looking at W124s again and W123s , just waiting for the right one to present itself .