While nice to look at most classics are a huge disappointment to drive. Forget power steering for starters, brakes that stop the car more than once, big engines that sound good but produce very little power by today's standards, positively lethal passenger cabins, handling that can be best described as " interesting" and lots of practical snags like getting tyres the right size that don't cost an arm and a leg or fuel that won't destroy the valves. About the only thing that might be better will be the ride quality.
So "try before you buy " would be my advice and don't go back further than the mid 80's unless you want to experience time travel.