I live in San Francisco, I rent a small apartment in a fairly nice neighborhood. Without fail, every night parked on the street are 2 Audi S5s[1], a Tesla Model S[2], an E63 AMG Wagon[3], and a smattering of Porsches (new Boxters to oldish 911's).

[1]http://www.motortrend.com/cars/2013/audi/s5/pricing/ (~$60k) [2]http://www.teslamotors.com/models/options (~$80k) [3]http://buyersguide.caranddriver.com/mercedes-benz/e-class/20... (~$100k)

Surprisingly it usually works out fine to park a totally empty $100k car on the street in SF, but if you leave $0.25 on the seat of a $500 toyota, some crackhead homeless fucker will break your window ($100-300 to fix it) to steal it.

It's not a supercar, but a guy in my neighborhood (in Los Angeles) parks his Bentley on the street.

Me, I'd clean out my garage if I had a Bentley.

Back when YC had demo days at YC's office, rather than at a nearby museum with a parking lot, there were a lot of amazing cars street parked for blocks. And at least one highly lulzy incident involving an SL65 and an asshole machinist dragging it with a forklift into the middle of a street.

There's a guy on my street (SF) who does the same thing. It seems either insane or haughty to me.

Surprisingly often. If not routinely, they absolutely do during the day when visiting places.

I've seen Johnny Ive's Aston Martin parked on the street in the Mission, along with more pedestrian 100k M5s, E63 AMGs, 911 Turbos, &c.

If you worry about parking on the street then you can't afford the car.