As a general rule it is too expensive and there may be too many issues with high milage cars. Paid service is almost out of the question locally. So buying a lower miilage examples in pretty good shape initially and keeping them up yourself should work out.

It is not only unreasonable but impractical as well to put older if not antique cars through our winter salt. It eats them alive. So in many ways this far north they have to be seasonal cars if you want some real remaining time out of them.

It is just my opinion but people that wamt to avoid doing their own work when required should not own old cars unless they have very deep pockets. Or the cars have very few issues. At least in general today new cars have no particular status advantage compared to years ago. In fact if they are in really good overall shape people may even envy owners that posses them.