Re painting, it's very difficult to match an old paint job. Even if you can get the same official shade (and they channge them every few years) manufacturing variation and/or wear & tear on the original finish (interior or exterior) will show. As a result trying to fix up the slightly cruddy bit turns into a major project.
Re the car, for many years I drove 2nd hand ones until the repair costs exceeded the value but our last one was shiny and new. If you can afford it get a new one, it's like going from biplanes to jets, remember you're driving an old bomb, not the Cutty Sark. An old car is only worth having if it's a restored classic (and I'd kill for a '57 Chevrolet or the Holden knock off of it) that you can look after and maintain yourself, otherwise it's a money pit.
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Re the car, for many years I drove 2nd hand ones until the repair costs exceeded the value but our last one was shiny and new. If you can afford it get a new one, it's like going from biplanes to jets, remember you're driving an old bomb, not the Cutty Sark. An old car is only worth having if it's a restored classic (and I'd kill for a '57 Chevrolet or the Holden knock off of it) that you can look after and maintain yourself, otherwise it's a money pit.