If money ( and storage space ) was no object…

Pretty simple. I'd start with what I already own:
1967 Barracuda convertible
1968 GTS convertible

To that I would add:
1962 300-H convertible
Jag XK-E roadster
Aston Martin convertible (would have to figure out which one)
1967 GTS convertible
1966 D/Dart
1966-67 Charger 383/AT/AC/power windows/etc.

BUT, at my age, I'm extremely satisfied with what I already own. I just need to finish them.