I bought a 66 Coupe (with the help of a knowledgeable family member) about 6 years ago. The seller made my family member feel comfortable enough to ok the purchase. That car made it 10 miles before dying.
Fast-forward to now. We’d found a piece of metal in the starter housing, needed a new radiator. Spent about $2500 to get her reasonable for driving. Moving to another state, had the car checked out as it had been a while since she’d been driven (I know). Spent another $3k on fuel tank...

66 Mustang - several issues