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I was born in the early nineties, definitely prefer the look of older generation Porsche models, and I am probably more interested in air cooled models (but that doesn't say it is the case for everybody of course).
Considering the success of Singer and other restomods my personal belief would be that older models will continue to be more looked for, but a younger generations could also mean cheaper budget and if old Porsche prices continue to skyrocket maybe they will target more affordable options (if we can say it like that) with more modern water cooled ones? -
In that case, of the choices you offered, as a child of the early 70s I'd go for a 993, the last of the air-cooled cars. The water-cooled cars are better for day-to-day use, but they're around in huge numbers whereas the air-cooled cars are more direct. No point in a 964 as that's really just the older Carrera with fugly bumpers, the 993 had much better rear suspension. So that would be my choice.
Daily driver, weekend fun car, or garage queen investment?