The flip side of the coin is that kids learn from a very early age what it takes to slip past the surveillance net. The smart ones watch everyone around them get caught for infractions. Taking note. Quietly gathering data. Towing the line, purposely being caught for the occasional minor infraction so as not to appear too good to be true. Until one day, they disappear from prison in the middle of a storm and take the entire foreman's investment portfolio with them.
This scenario ends up being fairly elitist. Everyone should be free, and not everyone can crawl to freedom through five hundred yards of shit-smelling foulness I can't even imagine -- or maybe I just don't want to. Five hundred yards... that's the length of five football fields; just shy of half a mile.
Google-Docs-as-chat is extremely common in schools. Tons of schools use Google docs so they're not blocked, permissions (who you can bring to a doc) are usually wide-open, and monitoring's non-existent if you don't attract attention.
Oh wait, I think there was a movie about this...