I've seen people do exactly this in cars, too. Fortunately the Phoenix urban area has several hundred miles of off-road paved trails.
I skate with a club group that includes some cyclists (small children being pulled in a bike trailer, etc.) Cyclists, having much larger wheels, can take some trails skaters can't, but there is one major problem - their wheels are inflated with air. When we do a long skate with cyclists, there is usually at least one flat-tire hold somewhere along the way. On one memorable run recently, three of our four cyclists blew tires.
Bicycles have been around for two hundred years. Can't they come up with a better system?