I have an interest in this topic. But I think the issue of kids playing in the street (skateboards or not) is due to the lack of areas set aside for kids to play. There is not one playground or recreation area inside the gates of our community. The HOA and community planners do not have a plan to build a play area inside the gate. I've asked a number of times about this topic. I always get the same answer - "There is a play area near the pool". This is an unacceptable answer.
Many of us decided to purchase a home in a gated community. Why should we send our children outside of these gates to play? Our HOA dues are going towards common areas outside of our gated community. I don't have children, but I support parents who don't want to send their children outside of the gates in which we all have decided to live.
Now for skateboarding and skateboarding props: If the kids are skateboarding in the water drainage and not on the streets - great. Skateboarding got its start on the streets and drainage ditches of California. As far as I'm concerned, the kids can have a ton of fun in the drainage ditch - as long as they are not breaking the law and leave the area in good condition.
The kids need to clean up after their fun. When I was a kid we used our skateboards to transport our props to and from the "designated skateboard area". Our neighborhood and surrounding areas do not have skateboard areas. This is another topic to look at. If kids do not have areas to play, they will play in the streets - dangerous. If kids are bored, from lack of things to do - trouble quickly follows.
We as a community and adults need to have a positive and interactive role with the kids and their parents on this issue. In my last neighborhood the relationship between the kids and adults was very negative. This led to vandalism, verbal altercations and a couple close calls of physical altercations (neither side was innocent). Say "Hello" to kids talk to them, but if they are doing something wrong talk to them or their parents. When we talk to the kids let's talk to them the same way we would want adults to talk to us if we were in their shoes.
This really comes down to all of us getting out of our houses and interacting (positively) with our neighbors. We have an awesome community, but making this a neighborhood depends on all of us.