here's how i see it. new cars will always be more expensive...and they WILL get old, and WILL exhibit problems. it's just a matter of picking a car that you're willing to keep for the long run. I've picked picked mine and am fine with fixing whatever problems that might arise, even major ones. I know some repairs will seem expensive, but i'm pretty sure whatever that repair is will be a LOT cheaper than getting a newer car that will eventually break down and will need repairs.
cheapest route is to pick a diesel
that you're willing to drive for a loooong time (immortal styling) and deal with it.
my picks: 87 300TD
95 S280... flood damaged...gutting everything and simplifying
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85 190E 2.3(SOLD)
86 230E (-->300D) sold
87 300D (-->300TD) sold
68 250S w/ a 615 and manual tranny (RIP)
87 300TD (SOLD)
95 S280 "The KRAKEN" (Turbo 2.9 602 transplant) traded
86 190E 2.3... current project