When looking at a new barn for my horse:
“How often are the stalls cleaned?”
“Do you have automatic fly sprayers?”
“How many bags of shavings do you use?”
“What do you feed? And how often?”
“Do you offer blanketing?”
“What type of footing does your arena have?”
“How often do you drag it?”
“How big is your turnout?”

When looking at a new apartment for myself:
“Is there hot water?”
“Was anyone murdered here?”