Should I be pedantic?

As I'm a newbie on this site, I'm still learning the ropes around here. Now, after finishing a few GAs, I have a few questions: Are the rules about activation and multiple wins absolute? Should I enforce them with a pedantic attitude?

I understand the need for the rules, and the philosophy behind them. After all, it's like I wrote them myself. Still, in my GAs so far, there's been a not-so-insignificant number of winners with small offences on their record.

There are two scenarios standing out:

1. The winner didn't activate a (trash) game more than a year ago.
2. The winner (probably entering multiple simultaneous GAs) won two copies of the same game within a few days last year.

According to the rules/FAQ/general community consensus, I should report these and ask for a re-roll.

I tried that.

After three days, and the re-roll ticket still pending, I became aware of the fact that winners may already have been punished by SG for previous misbehaviour, but there would be no way for me to know. So I had to choose, should I be pedantic and bother SG support with every little misbehaviour (which may already have been punished), or should I let the small fish slip through. I chose the latter, mostly because I couldn't create more new GAs since unfinished GAs held up my available spots, causing a queue to build up. Now, I'm allowed to have more simultaneous GAs, so I can reconsider my choice.

In a perfect world, I'd report and re-roll any offence against the two rules. But I'm not sure if the world is perfect enough.

What do you think? What do you do?