Is this a reference to something that happened?

This is a terrible idea for a multitude of reasons.

A: dozens of cars are tons of money, unless you plan on stealing them which is incredibly shitty to do and it’s exponentially risky

B: tow trucks exist, they’ll just move shit out of the way after a few hours

Finally why would you want to do this?

Most gated communities aren’t actually wealthy so you’re attacking the upper middle class at most.

Actually rich people don’t live in neighborhoods without guards so if you do try this against some 1%ers you’ll probably just end up slotted.