How old is the paint job? Very Important to know age.
Do you have a friend you can bring along that is knowledgeable on old cars?
You are in new york so be on the hunt for rust in the lower body, floors and frame rails.
Use weak magnets to find rust and filler, or get a depth gauge. I was selling a car and this gage a buyer brought could find out how deep the paint and Bondo was, very good tool to see what's under the resale red.