You’re applying what you know about modern pool ownership and construction to pool skating in abandoned pools in the 70’s and 80’s in a specific region of California.
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These pools were in abandoned/foreclosed houses. Otherwise, they’d be kicked out before they even got close to the pool. Obviously. And public pools? Come on. These are a few scrubby teenagers; not exactly a threatening scene, and easily scared away.
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“Draining” the pool is getting rid of the stagnant puddle in the bottom of an unused pool. This was usually done with buckets, just dumping it over the side. Usually a couple hundred gallons tops. It might take a while with buckets, but it’s doable. Toss down some sand or kitty litter to soak up what can’t be scooped and then sweep it up and out.
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These pools were usually concrete, with formed coping edges. There’s no modern lined pools; those wouldn’t skate well and probably don’t even have suitable transition for skating anyways.
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Stealing a small token from an abandoned house is pretty low-key in terms of petty theft.