Never had any trouble with Porsche ownership/parking in downtown Chicago. I had an indoor heated space I owned. Maybe not as big a deal in a warm climate.
The biggest problem is no where to work on your car. Most condo associations do not allow for car maintenance in the garage. Otherwise, my $16K 911 wasn't a big deal compared to the $50K, $75K, $100K+ cars roaming the city.
Well....there are the $500 cars that like to blow red lights...