You should do it. For a fair-weather car an old full-size convertible is a great choice. Everyone on the street will love you. The kids will love it. Choose wisely and it'll keep it's value. Plus, you avoid unexpected - I dunno - ABS module failures and whatever other nonsense happens to modern cars. Pushrod V8 + 3 speed automatic and not much else. :)
You've got through the early '70s to choose from - twenty-five-ish years of cars that are extremely well suited to moving a family around at a moderate speed. :)
I bought my old Fleetwood because I love old Fleetwoods, but the joy it (apparently) brings to everyone else really sweetens the deal. :)
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