Having managed a venue where there were people living there, it could be a nightmare with concerts. The thought tended to be "I'm booked to be out at 10, so it doesn't matter if we run a weenie bit over" which often would mean finishing at 10:20. But that's the concert. Then there's a speech, and "oh we'll just give you one more" and then everyone staying behind to chat, and the clearing up etc.
And at half-eleven, having just got everyone out when someone realises they've lost their car keys/car won't start/just need the toilet/have you seen their glasses etc and banging on the door to get back in.
And the caretaker has to be up at 5:30am the next day for the people that day.
And if you try being nice and saying "are you nearly finishing as you only booked to 10:30?" you'll always be told that it's the "last song" or "nearly done." Amazing how often the last song can run over 10 minutes.
Then when they get the bill with an extra hour they're ever so indignant because it wasn't their fault. It never is, and nor did they break that window even though you have it on CCTV....
So I have some sympathy with him doing it. I do think he handled it badly, however they may have had form.
Edited to add: And you're the one dealing with the complaints from the residents when they're woken up by the concert leaving too.