By nice house I mean really nice, worth at least a mill, maybe a few mill. Indoor pool, the works. Top of the range security system etc. But when you open the front door you're likely to find a drunk asleep there... would it still be worth it?

ETA: oh and if he was a nice drunk I'd give him a cup of coffee LOL but just for arguments sake, lets make him not nice!
That sounds like the scenario close to the city in lots of cities. London, New York Sydney, Madrid; they've all got bums sleeping on the footpath outside multi-million dollar real estate.

The thing is that I've found is that expensive suburbs can often be less child friendly than scruffier ones.
My suburb makes the news occasionally for drive-by shootings and the like but if one of my children does the bolt at the super-market or post office they're always stopped before they reach the door and returned to me. If people see me waiting to cross the road they stop their cars so I can go. When we visit the 'blue chip' suburbs no-one stops my little bolters and no-one has ever stopped so that we can cross a road.
One of my friends recently moved from one of the posher suburbs in London to a scruffy suburb and she's found the exact same thing. Her children are safer and happier in the dodgy suburb.

ETA - I think there's a happy medium between living in a suburb where people don't want your children to ride their bike on the street in case they ride to close to their car and scratch it and a suburb where you have to wear a bullet-proof vest to hang out the washing (and let's face it none of us live in Iraq so we don't really need the kevlar vest)

ETA 2 - why would you give a bum a cup of coffee? They would probably prefer a beer.