If I owned a ground-level urban building
Twice a day during slow hours I would barricade off one side of the stairs, the sidewalk in front of the building and any other fixtures. I’d probably even design the entrance with skateboarding in mind. Anyone could sign up with us (including a waiver) and pay an a la carte fee to be able to skateboard our entrance during these times. I’d make the security staff handle any administrative work for this, to build a relationship with the clients. Skateboarders that love street skating love skating on real streets, why not cater to them and make some money off it? It’ll happen anyways. Is this too blissfully ignorant or could this work?