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I'm confused.
What's the 996 and Mercedes for?
Or is this in the US? In which case route, road and traffic conditions will dictate the car.
Someone I know worked in OC, California and had a convertible for their stay... even there pollution and congestion meant they could never put the roof down.
In New York the roads are brutal, and almost every car is damaged, so an old Hilx or Outback would be my choice.
My defining criteria would include, air con, cruise control... and probably excellent safety give how poorly people drive.
As an investment it would be good as iirc if you own the car for >1yr you'll be able to import it back to the UK without paying tax. Then a weak £ should offer plenty of € buyers.
Putative 964 would be lhd, so a whole new world of fit possibilities