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I actually had a friend who would file every year on time but owed the CRA considerable money each year. He would do this for 4-5 years, and then when the amount owing was quite large (like over six figures) he would contact the CRA and negotiate a lesser settlement.
I even asked him why he bothered to file in the first place, and he said as long as you file they won't bother you too much (but they do want their money). It's the people who don't file are the ones they go after hard.
Kinda pisses you off that the ones who pay on time don't get any settled discounts eh!!!!
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