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I had stunt skates when i was a kid, and we built ramps and stuff to jump, and played hockey in the street.
I recently got me a nice comfortable pair to just ride around. It's fun, but not the best solution as far as transportation goes. I just drive on bike paths and empty roads outside of town, but i'd never go into town with them. You can't stop very well, you've got a wide swing, can't go into stores, wet/dirty surfaces are a no-no, etc...
I've got a crappy bike to go where i need to, and a nice pair of skates to go where i want to.