If the owner of the property is nice to you and asks you to not skate/destroy their property, do not skate it.
I've had a few people at businesses be pretty friendly and honest, so we basically struck a deal to not mess up their stuff.
Example: This guy had marble ledges put in (for landscape edges) and we walked up, drooling at it. He came out and said "I know you guys want to skate here, but can I ask you to please not. It cost me around $8000 etc etc". And we told him "Thanks for talking to us like adults, we won't ever skate this " and shook his hand. Never skated it.
We had a lawyer's office that let us skate the ledges by their front door while they were open. Will never forget that, had that spot for years. The new owner however parks their car there to block the ledges, so that is what it is.