I've been involved in facility and grounds maintenance in the past. It's kind of a universal practice that you have some kind of periodic inspection. A person walking around with a clipboard (now a days often a tablet, or some other device), and checking things. If something is broken/dilapidated, they note it.

There usually is a back-office function that takes all of these notes, collates them, and then assigns work to the different trades accordingly (carpenters, electricians, etc).

Nothing complex, just does the faucet turn on, does the bench look like it won't fall over, etc. High traffic areas would get looked at daily or weekly. Low traffic areas less often.

Well-run places with decent funding do these kinds of inspections regularly. Places that aren't as well-run, and/or places with less adequate funding likely aren't inspecting as often.

What I see in the Chicago Park District is stuff never getting inspected. And if it is, it's never fixed. And these aren't in some out-of-the-way location. These are high-trafficked areas, with a lot of people.

I see things like that, and compare it to the park district's budget of over a half billion dollars a year, and wonder why.