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Having been through this process once, I can safely say it does NOT get any easier. Each child is different. End of story. Here's what I've observed and learned over the course of having one child and now the second apply for postsecondary education.
The reality is that in Toronto, as in most police services across the continent, the vast majority of serving police officers are exceptional public servants. The bad news is that reality is entirely irrelevant. People don't form judgments or base their decisions and actions on reality. They base them on their perceptions. And a fast-growing segment of society in Toronto, in Chicago, in New York City, in Ferguson, in cities and towns across North America, perceive their police services to be acting for their own benefit -- not society's.
Every parent is unique, but we all share a common goal before we go tits-up: To die with no regrets. (Other than the regret of accidentally swallowing that rat poison that's now killing us.) And that pursuit -- or avoidance, rather -- is a complicated thing.