My partner occasionally fawns over the idea of buying a vintage Jeep, "just to drive around town, not on the highways". Safety has always been my #1 point of pushback, and when we looked into what can happen even in a low speed accident without modern safety systems, that idea was put to rest pretty quickly.
Driving old cars, especially open top, can be a really fun, joyful activity! Risk manage it like any other high risk activity: plan ahead, pay attention, and be realistic about your ability.