Scooters are to motorcycles like motorcycles are to cars.
The smaller turning radius of the scooter makes it much more agile than a motorbike.
You should be crazy to invest in a +20 year old motorbike that you'll be constantly fixing instead of riding, as opposed to buying a scooter and being done with it.
I've been riding an Aprilia Habana Custom through the streets of my city for 5 years now, and it's faster and cooler than any bigger bike in these conditions.
Obviously, it won't take me out of town, but that's what I've got a car for anyway.
And as far as brakes go, mine has two disk brakes. I don't think most 80's motorbikes do.
As for the sexual self-image, riding a motorbike in San Francisco, with that moustache and leather vest with no shirt... I don't know.