I think scooters don't compare well to larger motorcycles, myself. A motorcycle with a 650cc engine can be had for the money you're considering. The larger engine gives you much more flexibility in traffic. You can take it on the freeway, as well. Parking is no more difficult than with a scooter. And, myself, I think a motorcycle is way cooler...
Motorcycles don't compare in fuel efficiency though. I get about 44mpg on my motorcycle. A guy on a scooter will easily double that, maybe even ease into the triple digits.